Heterocyclic Building Blocks-Tetrahydropyrans

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,951127-25-6

2.46 kg of Compound III and 3.12 kg of Compound II were added to 15 L of N, N-dimethylacetamide, and nitrogenUnder guard,Circulating frozen saline bath to 5 ¡À 5 ,Added dropwise trimethyl orthoformate 2.2Kg,Sodium borohydride acetate was added in portions3.19Kg,Stirred at 5 ¡À 5 C for 2 hours,Heated to 50 ¡À 5 for about 10 hours;Circulating frozen saline bath to 5 ¡À 5 ,45 C below the drop in water 15L,Add Bi temperature at this temperature for 1 hour,Heated to 50 ¡À 5 C for 2 hours,Centrifuge,Wet product washed with water 5L three times,Wet product was added to the water 15L beating 1 hour,Centrifuge,50 C for 12 hours under vacuum.Get gray whiteSolid was added isopropyl ether 12L,Heated to 60 ¡À 5 ,Then add n-heptane 12L, cooled to 15 ¡À 5 , incubated for 1 hour,Suction filtered and dried under vacuum at 40 C for 12 hours to obtain 3.1Kg of white solid with a yield of 82.5%

As the paragraph descriping shows that 951127-25-6 is playing an increasingly important role.

Reference£º
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Ying Shuhuan; Pi Hongjun; Chen Jian; (14 pag.)CN106674227; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

951127-25-6, tert-Butyl N-[(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydropyran-3-yl]carboxylate(0.22 g, 0.67 mmol) was dissolved in N,N-dimethylacetamide (3.3 mL).Add 2-(2-thienylsulfonyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole 4-methylbenzenesulfonate (0.38 g, 0.89 mmol) at room temperature 10 minutes, nitrogen protection,Sodium triacetoxyborohydride (0.83 g, 3.93 mmol) was slowly added at 0 C.The reaction was resumed at room temperature for 12 hours.The reaction was quenched by the addition of aqueous ammonia/water (v/v = 2/3, 50 mL) and filtered.The obtained solid was purified by silica gel column chromatography [methanol / dichloromethane (v / v) = 1 / 9]The title compound was obtained (0.30 g, yield 79%).It is a brown foamy solid.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

693287-79-5, tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,693287-79-5

A mixture of tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate (3.8 g,0.018 mol) and trifluoroacetic acid (20 mL, 0.3 mol) were stirred in dichloromethane (20 mL) for 90 minutes. The mixture was concentrated, and the residue was taken up in acetonitrile (30 mL). l-(2,6-difluoropyridin-3-yl)propan-l-one (2.34 g, 0.0137 mol) was then added, and the resulting mixture was stirred at 75 0C for 72 hours. After cooling to room temperature, the mixture was concentrated, and the residue was purified by flash chromatography on silica gel using a 10-50% hexane:ethyl acetate gradient (flow rate 20 mL/min). The organics were combined and the crude product was then extracted with ethyl acetate. The combined extracts were washed with saturated sodium bicarbonate and then concentrated to afford 2.86 g (83.9 %) of 3-ethyl-6-fIuoro-l-(tetrahydro-2H-pyran- 4-yl)-lH-pyrazolo[3,4-b]pyridine as a white solid. LC/MS (EI) tR 3.5 (Method E), m/z 250 (M++1).

As the paragraph descriping shows that 693287-79-5 is playing an increasingly important role.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/44528; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

General procedure: To a flame-dried Schlenk tube was charged with vinyl bromide (0.30 mmol, 2 equiv, if solid), unactivated alkyl halide (0.15 mmol, if solid), zinc powder (16.5 mg, 0.30 mmol, 2 equiv), and MgCl2 (14.2 mg, 0.15mmol, 1 equiv). The tube was moved into a dry glovebox, at which point Ni(cod)2 (2.1 mg, 0.008 mmol, 5 mol%) was added. The tube was capped with a rubber septum, and it was moved out of the glovebox. At this point, the vinyl bromide (0.30 mmol, 2 equiv, if liquid) and alkylhalide (0.15 mmol, 1 equiv, if liquid) were added together with solvent (1 mL) and pyridine (11.8 mg, 0.15 mmol, 1 equiv) via a syringe.The mixture was stirred for 16 h under N2 atmosphere at 25 C, and then it was directly loaded onto a column (silica gel) without work-up. The residue in the reaction vessel was rinsed with small amount of CH2Cl2. Flash column chromatography provided the product as a solid or oil. The E/Z ratio of the product was determined by GC-MS. (E)-4-Styryl-1-tosylpiperidine (3): according to the general procedure, column chromatography (silica gel, 7% EtOAc/PE) gave the product (42.5 mg, 0.125 mmol, 83%) as a white solid; mp 140-141 C. 1H NMR (500 MHz, CDCl3): delta = 7.66 (d, J = 8.0 Hz, 2 H), 7.34-7.28 (m, 6 H), 7.20 (t, J = 7.0 Hz, 1 H), 6.31 (d, J = 16.0 Hz, 1 H), 5.97 (dd, J = 7.0,16.0 Hz, 1 H), 3.82-3.80 (m, 2 H), 2.44 (s, 3 H), 2.34-2.29 (m, 2 H), 2.08-2.02 (m, 1 H), 1.83-1.81 (m, 2 H), 1.73-1.70 (m, 1 H), 1.46-1.39 (m, 1 H). 13C NMR (125 MHz, CDCl3): delta = 143.4, 137.1, 133.4, 133.1, 129.5, 128.9, 128.5, 128.2, 127.7, 127.2, 126.0, 46.1, 38.5, 31.2, 21.5. HRMS (ESI): m/z [M + H]+ calcd for C20H24NO2S: 342.1522; found: 342.1525.

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gu, Jun; Qiu, Canbin; Lu, Wenbin; Qian, Qun; Lin, Kunhua; Gong, Hegui; Synthesis; vol. 49; 8; (2017); p. 1867 – 1873;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of lithium diisopropylamide (1.8 M in THF/heptane/ethylbenzne, 3.6 mL, 6.4 mmol) in 10 mL of THF at -78 0C was added trimethylsilyl chloride (1.4 mL, 11 mmol) dropwise via syringe pump. The product of Example 143B (1.0 g, 5.8 mmol) in 5 mL of THF was then added to the mixture dropwise via syringe pump. The mixture was stirred at -78 0C for 2 hours then N-bromosuccinimide (NuBS, 1.1 g, 6.0 mmol) in 10 mL of THF was added dropwise via syringe pump. The reaction mixture was allowed to warm slowly to ambient temperature and was stirred for 16 h. The mixture was then concentrated under reduced pressure and the residue was dissolved in 20 mL of EtOAc, washed 1 X 5 mL of H2O. The aqueous layer was extracted 3 X 5 mL of EtOAc and the combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 70% hexanes in EtOAc) to provide the title compound (0.70 g, 2.8 mmol, 48% yield). MS (DCIZNH3) m/z 268 (M+NH4)+., 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; WO2006/69196; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

To a stirred suspension of 3-bromo-N-(4-ethyl-phenyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (11, 2.20 g, 5.34 mmol)and Cs2CO3 (3.48 g, 10.7 mmol) in DMF (44 mL), was added 4-(bromomethyl)tetrahydropyran (1.15 g, 6.40 mmol). The reactionmixture was stirred at 80 C for 16 h, cooled to r.t. and quenchedwith water (5.0 mL). The reaction mixture was extracted withEtOAc (2 50 mL) and the organic phases were combined, washedwith a saturated solution of sodium carbonate, brine, dried overMgSO4 and concentrated to dryness. The residue was trituratedwith heptane and the solid obtained was collected by filtration anddried to a constant weight in a vacuum oven at 40 C to afford thetitle compound (2.36 g, 87%) as a white solid: UPLC-MS(tR 1.52 min, purity 100%), ESI m/z 510.11/512.11 (MH); 1HNMR (400 MHz, CDCl3) d 7.77 (d, J 2.3 Hz, 1H), 7.46 (dd, J 8.6,2.3 Hz, 1H), 7.21e7.09 (m, 2H), 7.04e6.93 (m, 2H), 6.87 (d, J 8.6 Hz,1H), 4.07 (ddd, J 11.6, 5.0, 1.8 Hz, 2H), 3.94 (d, J 6.4 Hz, 2H), 3.50(td, J 11.6, 2.1 Hz, 2H), 3.29 (d, J 7.3 Hz, 2H), 2.67 (q, J 7.6 Hz,2H), 2.19 (m, 1H), 1.83 (m, 2H), 1.67e1.49 (m, 2H), 1.26 (t, J 7.6 Hz,3H), 0.93 (d, J 6.6 Hz, 6H)., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lafitte, Guillaume; Parnet, Veronique; Pierre, Romain; Raffin, Catherine; Vatinel, Rodolphe; Musicki, Branislav; Tomas, Loic; Bouix-Peter, Claire; Ouvry, Gilles; Daver, Sebastien; Arlabosse, Jean-Marie; Boiteau, Jean-Guy; Gerfaud, Thibaud; Harris, Craig S.; Tetrahedron; vol. 74; 40; (2018); p. 5974 – 5986;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

720706-20-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.720706-20-7,(4-Amino-4-tetrahydropyranyl)methanol,as a common compound, the synthetic route is as follows.

Di-tert-butyl dicarbonate (6.39 g, 29.27 mmol) was added to triethylamine (3.70 g, 36.59mmol), (4-aminotetrahydro-2H-pyran-4-yl)methanol (3.2 g, 24.40 mmol) in THF (40 mL)under nitrogen. The resulting mixture was stirred at 70 C for 5 hours. The reactionmixture was quenched with water (50 mL), extracted with EtOAc (3 x 50 mL), the organic layer was then dried over Na2SO4, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford tert-butyl (4- (hydroxymethyl)tetrahydro-2H-pyran-4-yl)carbamate (4.20 g, 74%) as a white solid. ?HNMR (300 MHz, DMSO, 30C) 1.45 (9H, s), 1.50-1.84 (2H, m), 3.31-3.61 (6H ,m), 4.61- 4.66 (1H, m), 6.36 (1H, s). mlz (ES+), [M+H]+ = 232.

720706-20-7 (4-Amino-4-tetrahydropyranyl)methanol 18316484, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4295-99-2

Example 44 (Synthesis of 4-aminomethyltetrahydropyran hydrochloride) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 25L were charged 1685.8 g (containing 15.2 mol of 4-cyanotetrahydropyran) of 65.9% by weight 4-cyanotetrahydropyran-toluene solution, 8.8 kg of 5.86% by weight ammonia-methanol solution, 337.2 g (2.86 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D) and 2.1 L of methanol, and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61 MPa) at 50 to 60C for 7 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtrated material was washed with 2.0 L of methanol, and the filtrate and the washed solution were combined and concentrated under reduced pressure. To a reaction vessel made of glass equipped with a stirring device and a thermometer and having an inner volume of 3 L were charged said concentrate and 833 ml of tetraethylenepentamine, the mixture was stirred at 105 to 115C for 2 hours. After completion of the stirring, said solution was distilled under reduced pressure (70 to 80C, 1.73 to 4.67 kPa) to obtain 1430.2 g of the distilled solution containing 4-aminomethyltetrahydropyran. To a reaction vessel made of glass equipped with a stirring device, a thermometer and a dropping funnel and having an inner volume of 20 L were charged 8.3 L of n-butanol and 1232 ml (15.0 mol) of 37% by weight hydrochloric acid, and in a salt-ice bath, said distulled solution was gradually added dropwise to the mixture while maintaining a temperature of the mixture to 0C or therearound, and after completion of dropwise addition, the mixture was stirred at room temperature for 30 minutes. An operation that the resulting solution was concentrated under reduced pressure, and 5.0 L of n-butanol was added to the concentrate and further concentrated was repeated twice. Then, in a salt-ice bath, when the concentrate was stirred for 50 minutes, a solid was precipitated and filtered. The filtered material was washed with 1.7 L of toluene, and then, it was dried under reduced pressure at 60C to give 1692.9 g (Isolation yield: 73.6%) of 4-aminomethyltetrahydropyran hydrochloride as white crystals. Physical properties of 4-aminomethyltetrahydropyran hydrochloride are as follows. Melting point; 190 to 193C 1H-NMR (DMSO-d6, delta (ppm)); 1.13 to 1.26 (2H, m), 1.63 to 1.68 (2H, m), 1.78 to 1.92 (1H, m), 2.67 (2H, d, J=7.1Hz), 3.22 to 3.30 (2H, m), 3.82 to 3.87 (2H, m), 8.21 (3H, brs) CI-MS (m/e); 116 (M+1-HCl), 99

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; Ube Industries, Ltd.; EP1671937; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 1 Synthesis of 3-hydrazinocarbonylmethyl-5-methyl-hexanoic acid (III)A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5 C. A solution of 3-isobutyl-glutaric anhydride (50.0 g, 0.294 mol) in toluene (200 ml) is dropped therein in about 1-2 h, keeping the temperature below 0-5 C. The mixture is reacted for about 1 h, then the phases are separated, the aqueous phase is concentrated to small volume, thereby obtaining a white solid which is taken up into isopropanol (100 ml) and filtered. The solid is dried under vacuum at a temperature of 30-35 C. for 16-18 hours. 56.7 g of product are obtained, in an 86% yield.1H-NMR (300 MHz, D2O, 28 C.): delta 2.20-1.90 (m, 5H); 1.50 (m, 1H); 1.05 (m, 2H); 0.75 (d, 6H)., 185815-59-2

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Dipharma Francis S.r.l.; US2009/143615; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

KHMDS (1M in THF) (39.0 mL, 39.0 mmol) was added to THF (150 mL) at -78C under nitrogen. A solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (5 g, 39.0 mmol) in THF (20 mL) was added and the mixture was stirred at -78C under nitrogen for 1 .5h, giving a pale yellow solution. A solution of N-(5- chloropyridin-2-yl)-1 ,1 ,1 -trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide (15.32 g, 39.0 mmol) in THF (25 mL) was added over 20 minutes and the resulting orange, then colourless mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction was quenched with NaHCO3 and the crude product extracted with MTBE (300 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under vacuum. The residue was dissolved in a small amount of 10% EtOAc:lsohexane and loaded on a 40g column. The crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane). Fractions containing product were combined, filtered, washing with 10% EtOAc:lsohexane, then concentrated. A solid formed in the residue, which was then taken up in 10% EtOAc:lsohexane, filtered through cotton wool. The filtrate was then loaded on a 40g column and the crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane) to afford 1 -(tetrahydro-2H-pyran-4-yl)vinyl trifluoromethanesu Ifonate (6.17 g, 20.15 mmol, 51.7% yield) as a colourless oil. 1H NMR (CDCI3) O: 5.14 (dd, 1H), 4.94 (dd, 1H), 4.06 – 3.98 (m, 2H), 3.41 (td, 2H), 2.54 -2.41 (m, 1 H), 1.89 – 1.79 (m, 2H), 1.66 – 1.50 (m, 2H)., 137052-08-5

The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; HOWARD, Steven; CONS, Benjamin, David; ST. DENIS, Jeffrey, David; GRIFFITHS-JONES, Charlotte, Mary; HISCOCK, Steven, Douglas; HOLVEY, Rhian, Sara; BURNS, Alan, Richard; COUSIN, David; DEXTER, Hannah, Louise; PARRA, Guillaume, Francois; WATTS, John, Paul; JEWELL, Robert; STOCKWELL, Jennifer, Ann; HIRST, Kim, Louise; LEMASSON, Isabelle, Anne; NASH, David, John; OSBORNE, James, Daniel; PRIEDE, Jonas, Calleja; RICHARDS, Nicholas, Paul; DUMAS, Aaron, Michael; BISHOP, Brian, Christopher; PARRY-JONES, David; SCOTT, Jeremy, Peter; SHAUNMUGHAM, Meenakshi, Sundaram; MULLENS, Peter, Richard; LATHBURY, David, Charles; DIXON, Darren, James; GAUNT, Matthew, James; (291 pag.)WO2018/178691; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics