Heterocyclic Building Blocks-Tetrahydropyrans

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 2-chloro-N-i sopropyl -5 -(1 H-pyrazol-4-yl)pyridin-4-amine(200 mg, 0.845 mmol) in DMF (4 mL) was added Cs2CO3 (413 mg, 1.27 mmol) and 4-bromotetrahydro-2H-pyran (167 mg, 1.01 mmol). The reaction mixture was heated at160 C for 2.5 h under microwave irradiation. After cooling, the mixture wasconcentrated to dryness and then partitioned between EtOAc (150 mL) and ice water (20mL). The layers were separated and the organic layer washed again with cold water. Theorganic layer was dried over Na2SO4, filtered, and concentrated. The product was purified via column chromatography (30% EtOAc/pet ether) to afford 2-chloro-N- i sopropyl -5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H-pyrazol-4-yl)pyridin-4-amine (80 mg, 30% yield). LCMS 321.1 (M+H)., 25637-16-5

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; SANTELLA, Joseph B.; WU, Hong; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (72 pag.)WO2016/210037; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

B. 3- [5-AMINO-4- (TETRAHYDRO-PYRAN-4-CARBONYL)-IMIDAZOL-1-YL]-N- CYCLOPROPYL-4-METHYL-BENZAMIDE A solution of 4-bromo-tetrahydro-pyran (0.82g, 5MMOL) in dry THF (IOML) was added dropwise to the suspension of magnesium (132mg, 5.5 mmol) and iodine (25mg) in dry THF (20 mL) at 50 C under N2. The mixture was stirred for 30 min after addition at 50 C, then cooled to room temperature. Then a THF (LOML) solution of 3- (5-AMINO-4-CYANO-IMIDAZOL-1-YL)-N-CYCLOPROPYL-4-METHYL-BENZAMIDE (90 mg, 0.32 mmol) was added to the reaction mixture and it was stirred at room temperature for 3h then quenched with HC1 (2N) and stirred at room temperature overnight. The pH of the solution was adjusted PH-8 with saturated aqueous K2CO3 was and it was extracted with EtOAc. The organic layer was washed by water and brine, dried over NA2SO4, and concentrated. The crude product was purified by column chromatography on silical gel (EtOAc-EtOAc : MeOH: Et3N = 100: 10: 1), and the product was obtained as a beige solid (35 mg, 30 %)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; TRIAD THERAPEUCTICS, INC.; WO2005/9973; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

STEP 2. DIHYDRO-2H-PYRAN-3(4H)-ONE To a stirred mixture of pyridinium chlorochromate (11.02 g, 51.1 mmol) and 3 A molecular sieves (10.0 g) in DCM (100 mL) was added a solution of tetrahydro-2H-pyran-3-ol (3.48 g, 34.1 mmol) in DCM (100 mL). The reaction mixture was refluxed for 3 h before being cooled to room temperature and partially concentrated in vacuo. The mixture was then diluted with EtOAc and filtered through Celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography to give dihydro-2H-pyran-3(4H)-one., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; US2010/160280; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 To a solution of ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temeperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g)., 388109-26-0

As the paragraph descriping shows that 388109-26-0 is playing an increasingly important role.

Reference£º
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Gwaltney, II, Stephen L.; Harris, Jason R.; US2015/259296; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Oxidation of alcohol 49 (2.12 g, 20.8 mmol) with DMP (9.91 g, 23.3 mmol) in accordance with Method Y provides the pyranone 50 (1.78 g): 1H NMR (250 MHz, CDCl3, deltaH) 4.03 (s, 2H), 3.86 (app t, 2H), 2.54 (app t, 2H), 2.12 (m, 2H).; Method Y[0277] To a suspension of the 3-pyranol (1 equiv) and 4 A molecular sieves (2 g/g 3- pyranol) in DCM (5 mL/mmol) is added DMP (1 equiv) portionwise over 20 min. Reaction progress is monitored by TLC. Additional DMP (0.2 equiv) is added as required. After 1 h, the reaction mixture is partitioned between DCM and 2 M K2CO3. The organic phase is separated and the aqueous extracted with DCM (3 x). The combined organic phases are washed with brine, dried (MgSO4), filtered, and coned in vacuo. Column chromatography (silica gel, 1:2 EtOAc in heptanes) provides the 3-pyranones., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; PANACOS PHARMACEUTICALS, INC.; NITZ, Theodore, J.; SALZWEDEL, Karl; FINNEGAN, Catherine; BRUNTON, Shirley; FLANAGAN, Stuart; MONTALBETTI, Christian; COULTER, Thomas, Stephen; WO2009/85256; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of tosyl chloride (1.4 g, 7.34 mmol, 1.5 eq) in pyridine (5 mL) was added to a solution of tetrahydro-2H-pyran-4-ol (0.5 g, 4.9 mmol, and 1.0 eq) in pyridine (5 mL) at 0 C. The reaction mixture was stirred under nitrogen atmosphere, at room temperature for 4 h. After complete consumption of starting material, IN aqueous HC1 was added, diluted with water and extracted with ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2SC”4, filtered and solvents evaporated from the filtrate under reduced pressure to obtain tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate.

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); 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 METHYL (S)-3-ISOBUTYL-GLUTARATE (III) A 1 L three-necked round-bottom flask, under nitrogen atmosphere, is loaded with 3-isobutylglutaric anhydride (5.0 g; 29 mmol) of formula (II) and methyl isobutyl ether (MTBE) (100 ml). The resulting solution, kept at temperatures of about 20-25C, is added with methanol (2.5 g) and CAL-B Novozym 435 (2.5 g), and the solution is kept under stirring for about 3 h. After that, the enzyme is filtered off and the solvent is evaporated off. The resulting product has 85% enantiomeric purity.

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.

Reference£º
Patent; Dipharma Francis S.r.l.; EP1992609; (2008); 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.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 C or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94%). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+)., 103260-44-2

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

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (2014); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

To a solution of DIAD (2.0 equiv.) and triphenylphosphine (2.0 equiv.) in THF (0.24 M) was added tetrahydro-2H-pyran-3-ol (1.2 equiv.). The mixture was stirred for 10 min. methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.) was added. The mixture was stirred at ambient temperature overnight. Additional triphenylphosphine (2.0 equiv.) and DIAD (2.0 equiv.) were added, and the mixture was stirred overnight. The mixture was concentrated and purified by flash chromatography over silica gel (heptanes:ethyl acetate gradient) to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate in 39% yield. Purification was completed via chiral HPLC (EtOH/heptane)=15/85, 20 mL/min, AD column) to yield (S)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee) and (R)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee). LC/MS=368.2 (MH+), Rt=0.92 min. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.65 (ddd, J=12.81, 8.51, 4.11 Hz, 1H), 1.78-1.97 (m, 2H), 2.06-2.16 (m, 1H), 3.57-3.67 (m, 2H), 3.72-3.80 (m, 1H), 3.95 (dd, J=11.54, 2.15 Hz, 1H), 3.99-4.01 (m, 3H), 4.32 (dt, J=6.95, 3.37 Hz, 1H), 6.54-6.62 (m, 2H), 7.59-7.67 (m, 1H), 8.19-8.28 (m, 1H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); 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

Prepared as described by adaptation of the following literature reference: Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401 . To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2- methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. 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 18h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCI 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 toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+

14774-37-9, As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics