Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

In a 30 ml glass flask equipped with a stirrer, a thermometer and a dropping funnel, 1.0 g (9.0 mmol) of 4-cyanotetrahydropyran and 5 ml of dry tetrahydrofuran were added, and the liquid temperature was maintained at 0 to 5C.,10.8 ml (10.8 mmol) of a 1.0 mol/l lithium bis (trimethylsilyl)amide in tetrahydrofuran solution was gently added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. Then, 3.8 g (27 mmol) of iodomethane was added, the mixture was reacted at room temperature for 2 hours. After completion of the reaction, 15 mmol (15 mmol) of 1.0 mmol / l hydrochloric acid was added to the obtained reaction solution, under ice cooling, the reaction solution was concentrated. To the concentrate, 10 ml of a saturated aqueous sodium chloride solution was added, extracted twice with 30 ml of ethyl acetate, the extract was dried over anhydrous magnesium sulfate. After filtration, the concentrate was distilled under reduced pressur to obtain 0.98 g of 4-methyl-4-cyanotetrahydropyran (isolation yield: 87%) as light yellow liquid., 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NISHINO, SHIGEYOSHI; HIROTSU, KENJI; SHIMA, HIDEYOSHI; IWAMOTO, KEIJI; HARADA, TAKASHI; (13 pag.)JP5673729; (2015); B2;,
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.

solution of 3,5-difluorophenol (1.15 g, 8.81 mmol), tetrahydro-2H-pyran-3-ol (0.900 g, 8.81 mmol), triphenylphosphine (2.31 g, 8.81 mmol) and DIAD (1.74 mL, 8.81 mmol) in THF (10 mL) was stirred overnight. The solution was then concentrated under reduced pressure and the residue was purified by purified by column chromatography on silica gel using CombiFlash apparatus eluting with EtOAc/hexanes (0-30%). The purification afforded 1.43 g (75.8%) of the sub-title compound as a colorless oil., 19752-84-2

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

Reference£º
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Synthesis of 3-Methoxy-4-(tetrahydro-pyran-4-ylmethoxy)-benzonitrile (For Example1 .0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)- tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time,1 .1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (Si02: ethyl acetate/heptanes: 10% to 30%) provided the title compound. Yield: 307 mg (19% of theory)Analysis: HPLC-MS (Method B): Rt: 1 .85 min., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1152567-60-6, 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of 4-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-tetrahydro- pyran-4-carboxylic acid To a mixture of 1-20 (91 mg, 0.32 mmol), R-8 (95 mg, 0.38 mmol),bis(triphenylphosphine)palladium(II)dichloride (27 mg, 0.03 mmol) in THF (2.0 mL) at room temperature is added KC03 (128 mg, 1.3 mmol), and H20 (0.3 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to roomtemperature, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in CH2C12) to give the title intermediate 1-32 (83 mg).

1152567-60-6, The synthetic route of 1152567-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

28244-94-2, 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3: To a solution of 2 (32.6 g, 71.8 mmol) in 500 mL of dry MeOH was added catalytic amount of sodium methoxide (NaOMe) and stirred for 3 h at ambient temperature. The reaction was neutralized by adding Amberlite IR-120 and filtered, the resulting solution was concentrated to dryness to give 3 (20.3 g, 99%) as white solid, which was directly used for next reaction without further purification. 11 NMR (MeOD, 600 MHz) delta 7.46 (2H, d, J=7.8 Hz), 7.12 (2H, d, J=7.8 Hz), 4.50 (1H, d, J=9.6 Hz), 3.85 (1H, d, J=12.6, 1.8 Hz), 3.66 (1H, dd, J=12.0, 5.4 Hz), 3.36 (1H, t, J=9.0 Hz), 3.24-3.28 (2H, m), 3.17 (1H, t, J=9.0 Hz), 2.13 (3H, s). 13C NMR (MeOD, 150 MHz) delta 138.90, 133.66, 131.33, 130.67, 89.79, 82.16, 79.81, 73.82, 71.50, 63.03, 21.24. HRMS (ESI-TOF) for C13H18O5SNa+ [M+Na]+ calcd 309.0767. found 309.0772.

28244-94-2, The synthetic route of 28244-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WONG, Chi-Huey; Yu, Alice L.; Lin, Kun-Hsien; Chen, Tai-Na; US2015/71960; (2015); 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.

5-Bromo-2-oxo-1,2-dihydropyridine-3-carboxylic acid methyl ester (2.3 g, 10 mmol, 1.0 eq) was dissolved in DMF (30 mL), and 4- (bromomethyl) tetramethyl was added Hydrogen-2H-pyran (2.15 g, 12 mmol, 1.2 eq) and potassium carbonate (4.15 g, 30 mmol, 3.0 eq). The mixture was heated to 60 C and stirred for 4 hours. After the reaction was detected by LC-MS and TLC, the temperature was lowered to room temperature, suction filtered, the mother liquor was poured into water (50 mL), and EA (50 mL ¡Á 3) was extracted. The organic phases were combined, washed with saturated brine 3 times, dried, filtered, and concentrated. The crude product was purified by silica gel column chromatography (100-200 mesh silica gel, PE / EA = 0-50%) to obtain an off-white solid (1.8 g, yield: 55%).

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

Reference£º
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Wan Zhonghui; (107 pag.)CN110041316; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

28244-94-2, 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 22.0 g (48.4 mmol, 1 eq.) 4-methylphenyl-2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside (2) in 50 mL methanol were added 800 mg (14.8 mmol, 0.3 eq.) sodium methanolate at room temperature. After complete conversion within 12 h, the reaction mixture was neutralized with Amberlite IR120 and the solvent was removed under reduced pressure. The crude product was co-evaporated with toluene (2 ¡Á 20 mL) and was used without further purification., 28244-94-2

As the paragraph descriping shows that 28244-94-2 is playing an increasingly important role.

Reference£º
Article; Johannes, Manuel; Reindl, Maximilian; Gerlitzki, Bastian; Schmitt, Edgar; Hoffmann-Roeder, Anja; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 155 – 161;,
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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

Thionyl chloride (10.0 mL, 137 mmol) was added to oxane-4-carboxamide (3.0 g, 23 mmol) and thereaction mixture was refluxed for 4 h, after which the reaction mixture was poured over ice andbasified to pH 14 with NaOH (50percent). The aqueous solution was extracted with EtOAc (3 ¡Á 50 mL),dried (Na2SO4) and concentrated in vacuo to give the product as a pale yellow oil (2.4 g, 94percent). Theproduct obtained did not require any further purification.IR numax 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011 cm?1;1H-NMR (CDCl3, 500 MHz): 3.91 (2H, ddd, J 11.9, 6.3, 3.6, 2¡Á2-HA), 3.61 (2H, ddd, J 11.9, 7.8, 3.3,2¡Á2-HB), 2.91?2.85 (1H, m, 4-H), 1.99?1.92 (2H, m, 2¡Á3-HA), 1.91?1.84 (2H, m, 2¡Á3-HB);13C-NMR (CDCl3, 75 MHz): 121.2, 65.6, 28.9, 25.3;HRMS (ESI+): Calculated for C6H10NO ([M+H]+): 112.0756. Found: 112.0754, Delta ?1.8 ppm.

344329-76-6, As the paragraph descriping shows that 344329-76-6 is playing an increasingly important role.

Reference£º
Article; Craven, Philip; Aimon, Anthony; Dow, Mark; Fleury-Bregeot, Nicolas; Guilleux, Rachel; Morgentin, Remy; Roche, Didier; Kalliokoski, Tuomo; Foster, Richard; Marsden, Stephen P.; Nelson, Adam; Bioorganic and Medicinal Chemistry; vol. 23; 11; (2015); p. 2629 – 2635;,
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 vial charged with 2A (0.624 g, 1.591 mmol) and 4-(bromomethyl)tetrahydropyran (0.427 g, 2.386 mmol) in DMF (3.98 ml) was added cesium carbonate (1.555 g, 4.77 mmol). The vial was capped and stirred at 75 C ON. The reaction mixture was poured into a separatoryfunnel containing water and ethyl acetate. The aqueous layer was extracted with ethylacetate (3 x). The combined organics were washed with 10% lithium chloride solution (4x), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The cmderesidue was purified by column chromatography on the Isco system (80 g, 0 – 10%MeOH/CH2C12) providing 5A (0.3973 g, 0.810 mmol, 50.9% yield). MS(ESI) m/z 490.3(M+H)., 125552-89-8

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); 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.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

Intermediate 427-chloro-5-(6-chloropyrimidin-4-yloxy)-2-(tetrahydro-2H-pyran-4-yl)-1H-benzo[d]imidazole Step 1: N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide; 0.40 g (2.12 mmol) 4-amino-3-chloro-5-nitrophenol were placed in 5 mL DCM. 0.44 mL (2.54 mmol) DIPEA and 0.26 mL (2.54 mmol) tetrahydro-2H-pyran-4-carbonyl chloride were added and at RT the mixture was stirred for 2 h. A further 0.26 mL (2.54 mmol) tetrahydro-2H-pyran-4-carbonyl chloride were added and the mixture was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with water. The organic phase was evaporated down i.vac.Yield: 0.60 g (94% of theory)ESI-MS: m/z=299 (M-H)- Rt(HPLC): 0.87 min (method B), 40191-32-0

As the paragraph descriping shows that 40191-32-0 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/88755; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics