Category: Tetrahydropyrans

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a round bottom flask under argon was placed tetrahydrofuran (30 mL) and 1,1,1,3,3,3-hexamethyldisilazane (1.50 mL, 7.13 mmol) and it was cooled to -78 C. in a dry ice/acetone bath. To this cooled solution was then added n-butyl lithium (2.5 M solution in hexanes, 2.70 mL, 6.69 mmol) and it was stirred for 15 min at -78 C. To this cooled solution was then added a solution of (3-methyl-4-methylsulfanyl-phenyl)-acetic acid methyl ester (1.34 g, 6.37 mmol) in tetrahydrofuran (20 mL) dropwise. This was then stirred for 10 min at -78 C. then at 0 C. for 1 h which resulted in an gold colored solution. After such time, the reaction was cooled back to -78 C. and a solution of 4-iodomethyl-tetrahydro-pyran (prepared as in PCT WO 2003/095438 A1, Example 20, 1.73 g, 7.64 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.17 mL, 9.56 mmol) was added dropwise at -78 C. The reaction was then allowed to slowly warm to 0 C. and it was stirred for 16 h. After such time, the reaction was diluted with ethyl acetate (250 mL) and washed with a saturated aqueous ammonium chloride solution (1¡Á50 mL) followed by a saturated sodium chloride solution wash (1¡Á50 mL). The organics were dried over sodium sulfate, filtered and then concentrated with silica gel (4 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 10% ethyl acetate/hexanes) to afford 2-(3-methyl-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (1.49 g, 76%) as a gold oil., 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2,61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 30 4-(4-bromo-3-chlorophenyl)-1-methyl-1,2,4,9-tetrahydropyrano[3,4-b]pyrazolo[4,3-e]pyridine-3,5(6H,8H)-dione 2H-Pyran-3,5(4H,6H)-dione (0.057 g, 05 mmol), 3-chloro4-bromo-benzaldehyde (0.11 g, 0.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.056g, 0.5 mmol) were processed as described in Example 26C to provide 0.145 g of the title compound. 1H NMR (300 MHz, DMSO-d6)6 3.5 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.92 (s, 1H), 7.03 (dt, 1H), 7.32(t, 1H), 7.6 (dd, 1H), 9.62 (s, 1H), 10.1 (s, 1H); MS (ESI-) m/z 410 (M+H:) Anal. calcd for C16H13N3BrClO3: C, 46.80;H,3.19; N, 10.23. Found: C, 46.77;H, 3.43; N, 10.27.

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

A solution of 2,2-dimethyltetrahydropyran-4-one (133) (115 g, 0.9 mol, 1.0 eq.) in anhydrous THF (600 mL) was cooled to -78 C and to it was added LDA (2.0 M, 538 mL, 1.08 mol, 1.2 eq.) drop wise under N2 keeping the internal temperature below -65 C. The resulting solution was stirred at -78 C for 20 min. A solution of N-phenyl- bis(trifluoromethanesulfonimide) (353 g, 0.99 mol, 1.1 eq.) in anhydrous THF (1900 mL) was added to the above solution slowly keeping the internal temperature below -65 C. The reaction mixture was warmed to room temperature slowly and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with MTBE (2 L X 2). The combined organic layers was washed with 10% aqueous NaOH solution (1 L X 2), brine (500 mL X 2), dried over Na2S04, filtered and concentrated to give crude title triflate product mixture as dark brown oil. The crude product was extracted with hexanes (2 L X 5) and the combined hexanes extracts was purified by column chromatography (directly loaded onto silica gel, Hexanes? 15% ethyl acetate in hexanes, R/= 0.6, visualized with KMn04 stain) to give 200 g of the triflate product mixture (134) (a mixture of 2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate ratio = 80.6: 19.4 by GCMS) as a light yellow liquid (~ 90% purity by GC-MS and 1H NMR). This was taken to the next step without further purification.

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of B-3Prepared as described by adaptation of the following literature reference:Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of compound B-2 in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2- methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aqueous HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L).Drying under reduced pressure at 40 C gave 216 g of compound B-3 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; *H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 – 1.35 (2 H, m), 1.54 – 1.63 (2 H, m), 1.85 – 2.02 (1 H, m), 2.45 (3 H, s), 3.28 – 3.39 (2 H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2 H, dd, J=l 1.37, 4.52 Hz), 7.35 (2 H, d, J=9.29 Hz), 7.78 (2 H, d, J=8.31 Hz)

14774-37-9, 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of intermediate A (O. lg, 0.47mmol), 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (2eq) in DMF (3mL) was stirred at 80C for 18h. LC-MS indicated that the reaction was not complete so further 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (leq) were added and the mixture stirred at 80C for 24h. Further 4- chlorotetrahydro-2H-pyran (2eq) and potassium carbonate (2eq) were again added and the mixture stirred at 80C for 72h. After cooling to rt, the mixture was treated with H20 and extracted with dichloromethane. The organic phase was collected and dried using a hydrophobic frit then concentrated in vacuo. The resultant residue was purified by prep. HPLC to give the title product. 1H NMR (d6-DMSO) delta 9.77 (s, 1H), 8.90 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 4.84 (s, 1H), 4.02 (dd, 2H), 3.84 (s, 3H), 3.58 (t, 2H), 2.20 (td, 2H), 1.90 (dd, 2H); LC-MS method B, (ES+) 300, RT = 6.36 min.

1768-64-5, The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLZOME LIMITED; HARRISON, Richard, John; OXENFORD, Sally; HOBSON, Andrew; RAMSDEN, Nigel; MILLER, Warren; WO2011/134831; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

624734-17-4, To a solution of the product from Step A (50 mg, 0.39 mmol) in methylene chloride (15 mL) was added Intermediate 4 (128 mg, 0.32 mmol) and N, N-DIISOPROPYLETHYLAMINE (203 uL, 1.17 mmol). After adding molecular sieves (15 mg), sodium triacetoxyborohydride (827 mg, 3. 9 mmol) was added and mixture stirred overnight. The mixture was extracted with methylene chloride, washed with sodium bicarbonate, dried under sodium sulfate and concentrated in vacuo. The crude product was purified on preparation plates (10/89/1, methanol/methylene chloride/ammonium hydroxide). 4 N hydrochloric acid was added and the solution was concentrated in vacuo to yield Example 2 (40 mg, 28%). LC-MS: MW calculated 443.24, found 444.5.

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK & CO., INC.; WO2005/14537; (2005); A2;,
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 7: Preparation of f3R)-5-methyl-3-(2-oxo-2(ralphaR)-l-phenylethyl1amino)ethvn hexanoic acid compound (24); [0081] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with ethyl acetate (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-5 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethyl acetate (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5C. The solvent was stripped off and the residue was extracted with 2.5-3 percent aqueous solution of NaHCO3 solution (500 ml), and diluted with water (1000 ml) followed by washing the aqueous phase with toluene (1 x 100 ml and 1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12 N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 26.6 g (61.5 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2- {[(lR)-l-phenylethyl]amino}ethyl)hexanoic acid with an optical purity of 99.3 percent, as measured by chiral HPLC.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); 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.713-95-1,6-Heptyltetrahydro-2H-pyran-2-one,as a common compound, the synthetic route is as follows.,713-95-1

4,4-Diethoxybut-1-yne 5 (6.66 g, 44.1 mmol) in dry THF (120 mL) was cooled to -78 C. nBuLi (27.7 mL of a 1.59 M solution in hexanes, 44.0 mmol) was added dropwise (2 min), which gave a pale yellow solution, that was stirred (10 min). A solution of delta-dodecalactone 4 (6.99 g, 35.2 mmol) in dry THF (30 mL) was added dropwise (5 min) and the solution was stirred (1 h). The reaction was quenched with saturated aqueous NH4Cl and allowed to warm to room temperature. This mixture was diluted with EtOAc and H2O and the organic layer was separated. The aqueous phase was re-extracted (2 times) with EtOAc. The combined organics were washed sequentially with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes, gradient; 10:90, 15:85; 25:75 then 30:70) to yield alkyne 6 (10.8 g 90%) as a clear yellow oil: Rf 0.34 (30:70 EtOAc/hexanes); IR (neat) 3448, 2937, 2858, 2217, 1674, 1457, 1373, 1346, 1228, 1162, 1120, 1063 cm-1; 1H NMR (CDCl3, 400 MHz) delta 0.85-0.90 (m, 3H, CH3), 1.20-1.25 (m, 6H, 2 X O-CH2-CH3), 1.25-1.53 (m, 15H), 1.61 (b s, 1H, OH), 1.66-1.89 (m, 2H), 2.58 (t, J = 7.2 Hz, 2H), 2.70 (d, J = 5.6 Hz, 2H), 3.51-3.61 (m, 2H) 3.64-3.73 (m, 2H), 4.70 (t, J = 5.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 14.02, 15.12, 20.00, 22.58, 25.39, 25.59, 29.22, 29.57, 31.76, 36.47, 37.45, 45.25, 62.08, 71.36, 81.73, 89.25, 100.96, 187.95; HRMS (EI) m/z 339.2516. C20H35NO4 [M-1] +¡¤ requires 339.2530.

As the paragraph descriping shows that 713-95-1 is playing an increasingly important role.

Reference£º
Article; Eldridge, Cecily; Quek, Gracia; Sako, Michael; Ryan, John H.; Saubern, Simon; Chebib, Mary; Macdonald, James M.; Tetrahedron; vol. 74; 12; (2018); p. 1245 – 1252;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 tert-Butyl (3R,4R)-4-(7-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-ylcarbamoyl)thieno[3,2-d]pyrimidin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate To a suspension of N-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-chlorothieno[3,2-d]pyrimidine-7-carboxamide (0.13 g, 0.38 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.12 g, 0.56 mmol) in dioxane (3 mL) was added DIPEA (0.20 mL, 1.12 mmol). The reaction mixture was heated at 115 C. overnight. The reaction mixture was cooled then diluted with EtOAc, washed with aqueous sodium carbonate, then brine, and then dried over anhydrous Na2SO4. The organic phase was concentrated and purified by chromatography (silica, 40 g, EtOAc) to give tert-butyl (3R,4R)-4-(7-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-ylcarbamoyl)thieno[3,2-d]pyrimidin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (0.065 g, 0.12 mmol, 32.3%) as a white solid. LCMS m/z [M+H]=538., 1240390-36-6

1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-20-7

5-Ethyl-1 -methyl-1H-pyrazol-3-amine hydrogen chloride (1/1) (purchased from Enamine, 1.00 g, 6.19 mmol), 4-(2-bromoethyl)oxane (CAS 4677-20-7, 310, 2.1 mmol), potassium carbonate (1.14 g, 8.25 mmol) and potassium iodide (34.2 mg, 206 pmol) were dissolved in 1 1 ml_ acetonitrile and the mixture was stirred for 10 min at 1 10’O in the microwave. The reaction mixture was cooled down to rt and concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layers were filtered through a waterresistant filter and the filtrate was concentrated under reduced pressure. The crude product was purified by HPLC under basic conditions to give 220 mg of the title compound (88% purity). LC-MS (Method2): Rt = 0.92 min; MS (ESIpos): m/z = 237 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm] = 1.04 – 1.26 (m, 5H), 1.40 (q, 2H), 1.50 – 1.62 (m, 3H), 2.40 – 2.48 (m, 2H), 2.96 (br t, 2H), 3.25 (td, 2H), 3.46 (s, 3H), 3.81 (dd, 2H), 4.79 (br s, 1H), 5.22 (s, 1H).

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; MORTIER, Jeremie, Xavier; MCCARREN, Patrick, Ryan; SERRANO-WU, Michael, H.; LEMKE, Chris; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (464 pag.)WO2019/96914; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics