Heterocyclic Building Blocks-Tetrahydropyrans

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.

General procedure: A solution of trimethyl phosphonoacetate (9.36 mmol) in THF (7 mL, 1.34 M) was added dropwise to sodium hydride (60% in mineral oil, 9.75 mmol) suspended in THF (35 mL) at 0 C. After 40 min, the pyranone (7.80 mmol), in THF (7 mL, 1.11 M), was added dropwise and the flask was heated to 25 C. After 19 h, the mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl (10 mL). The precipitate was removed by filtration and the layers were separated. The aqueous layer was extracted with ether (2*20mL) and the organic fractions were combined, dried (MgSO4), filtered, and concentrated under vacuum. The crude material was purified as indicated., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

720706-20-7, (4-Amino-4-tetrahydropyranyl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,720706-20-7

The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford 2-isopropyl-1-aza-3,8-dioxaspiro[4.5]decane

The synthetic route of 720706-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Corporation; US6353006; (2002); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 (50%). 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, 94%). 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

The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

5- (4-Fluorophenyl) -4-oxo-1,4-dihydropyridazine-3-carboxylic acid ethyl ester (500.0 mg, 1.9 mmol, 1.0 eq) was dissolved in DMF (5 mL) and added Cesium carbonate (1.85 g, 5.70 mmol, 3.0 eq) and 4-bromotetrahydro-2H-pyran (628.7 mg, 3.81 mmol, 2.0 eq) were stirred at 120 C for 5 hours. The reaction was monitored by TLC, and the reaction was concentrated under reduced pressure. Ethyl acetate (15 mL) and water (20 mL) were added, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate). Esters = 8: 1 to 2: 1) to obtain the product (342.0 mg, yield: 51.9%).

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

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

Under argon, 1.66 ml of 1,1,1,3,3,3-hexamethyldisilazane are dissolved in 20 ml of tetrahydrofuran. With ice cooling, 2.90 ml of n-butyllithium (2.5 M in n-hexane) are added dropwise, and the mixture is stirred at 0 C. for another 30 minutes. At -78 C., this solution is then added dropwise to a stirred solution of 2.0 g of ethyl (10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acetate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at -78 C. for 20 minutes, and 2.0 g of 4-(iodomethyl)tetrahydro-2H-pyran are then added dropwise. The cooling bath is removed and the mixture is allowed to slowly warm to room temperature. The reaction mixture is stirred at room temperature overnight. 10 ml of water are then added, the tetrahydrofuran is removed under reduced pressure and the residue is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate (100%:0%)=>n-heptane:ethyl acetate (0%:100%). This gives 2.0 g of ethyl 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionate as a colorless solid. C23H27NO5S (429.54), LCMS (ESI): 430.2 (M+H+).

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; SANOFI-AVENTIS; US2009/325942; (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.1152567-60-6,4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 82 O4-[4-((E)-2-Cyano-ethenesulfonyl)-phenyl]-tetrahydro-pyran-4-carboxylic acidTo a solution of l-(4-bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid (2.85 g, 10 mmol) in anhydrous THF (100 ml) under nitrogen at – 80 C (ether/dry ice), was added slowly Phenyl lithium in toluene 1.8 M (7 mL, 12.5 mmol). After 5 min, to this mixture, n- BuLi (2.5 M in hexane) (5.2 mL, 13 mmol) was added. A cloudy suspension was slowly formed. Twenty minutes after BuLi addition, a stream of sulfur dioxide was bubbled through the mixture for 15 min. The reaction mixture was then allowed to warm up to room temperature and the solvent was removed in vacuo. The sulfmate residue was dissolved in water (15 ml), acetic acid (8 ml), and MeOH (20 ml), followed by addition of 2-chloroacrylonitrile (1.3 g, 15 mmol). The resulting mixture was stirred at room temperature overnight. The organic solvents were removed and the residue was diluted with 20 ml of water. The solution was adjusted to pH5-6 with sat. K2HP04 aq. solution, then extracted with dichloromethane (2×50 ml), dried over MgS04. After filtration, the filtrate was stirred with triethylamine (2.8 mL, 20 mmol) for 1 h. The solution was washed with 10% aq citric acid and brine, dried over MgS04. The final product was purified by flash column chromatography (silica gel, dichloromethane/Ethyl acetate, gradient) to give 4-[4-((E)-2-Cyano-ethenesulfonyl)-phenyl]-tetrahydro-pyran-4- carboxylic acid (0.87 g, 27%) as a white solid. LCMS (ESI): m/z = 276 (M-C02H)+; 1H- NMR (DMSO-d6, 400 MHz) delta 13.00 (s, 1H), 8.23 (d, 1H, J = 15.7 Hz), 7.91 (d, 2H, J = 8.7 Hz), 7.74 (d, 2H, J = 8.7 Hz), 6.92 (d, 1H, J = 15.7 Hz), 3.82 (m, 2H), 3.48 (m, 2H), 2.40 (m, 2H), 1.88 (m, 2H); 13C-NMR (DMSO-d6, 100 MHz) delta 174.3, 150.2, 149.0, 136.1, 128.4, 127.6, 114.6, 112.2, 64.6, 48.5, 33.7., 1152567-60-6

1152567-60-6 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid 43119054, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; CEPHALON, INC.; UNIVERSITY OF HAWAII; UNIVERSITY OF UTAH RESEARCH FOUNDATION; DORSEY, Bruce; KUWADA, Scott K.; THEROFF, Jay P.; ZIFICSAK, Craig A.; WO2012/116151; (2012); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 mol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried overNa2504, filtered and concentrated. The residue was purified by preparative TLC (EAIMeO H =20/1) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahyd ro-2H-pyran-3- carboxamide (130 mg, 50percent yield)., 873397-34-3

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (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.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

A solution of 1 Hg (11.53 g, 35.03 mmol)Was dissolved in dichloromethane (130 mL) and cooled to 0 C. Dess-Martin periodinane (29.72 g, 70.06 mmol) was added portionwise to the reaction solution and allowed to warm to room temperature for 4 hours The Down to 0 C,The saturated sodium bicarbonate solution (60mL) was added dropwise to the reaction solution, stirred for 20 minutes, filtered, the filtrate was allowed to stand and the aqueous phase was extracted with methyl tertiary butyl ether (60 mL chi 3) (30 mL chi 2). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (petroleum ether / ethyl acetate (nu / nu) = 10: 1 – 4: 1) to give white crystalline powder intermediate 1 (10.85 g, yield 94.7%), 1172623-99-2

As the paragraph descriping shows that 1172623-99-2 is playing an increasingly important role.

Reference£º
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; FAN, JIANG; FENG, JIAN-CHUAN; PENG, FEI; CHEN, QING-PING; (89 pag.)TW2017/8224; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Preparation 8: Triphenyl(tetrahydropyran4-ylmethyl)phosphonium iodide; PPh,iA mixture of Preparation 7 (350g5 1.55M) and triphenylphosphine (406g, 1.55M) in acetonitrile (1.6L) was heated under reflux. After 27h the mixture was cooled and filtered, washed with diethyl ether and dried in air to provide a white solid (504g). Filtrate and washings were returned to reflux and concentrated to 750mL, reflux was maintained for 16h before cooling and dilution with diethyl ether (ca 1,2L). A precipitate formed which was stirred for 30min before being filtered, washed with diethyl ether (2 x 300mL) and dried in air to yield a further crop (lOOg). Overall yield of the title compound (604 g, 80%). RT = 2.7min; m/z (ES+) = 361.2.

101691-94-5, The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROSIDION LIMITED; WO2006/16178; (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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

2-Propyl-lH-imidazo[4,5-c]quinolin-l-ol (0.4 g, 1.8 mmol), 4- chlorotetrahydropyran (0.4 g, 3.3 mmol), and l,8-diazabicyclo[5.4.0]undec-7-ene (0.4 g, 2.6 mmol) were combined in a pressure vessel. The vessel was sealed and then heated in an oven at 120 0C for 22 hours. The reaction was repeated on a larger scale (x8). The small and larger scale reaction mixtures were combined and then partitioned between dichloromethane (150 mL) and saturated aqueous sodium carbonate (25 mL). The organic layer was separated, washed with water (3 x 25 mL), dried over potassium carbonate, filtered, and then concentrated under reduced pressure to provide 4.8 g of crude product as a brown oil. This material was purified by column chromatography (silica gel eluted with 5% methanol in dichloromethane containing 5 mL of ammonium hydroxide per liter of dichloromethane) to provide 0.98 g of 2-propyl-l-(tetrahydro-2//-pyran-4-yloxy)-l/-r- imidazo[4,5-c]quinoline as a yellow oil. HRMS (ESI) calcd for Ci8H2IN3O2 + H+: 312.1712, found 312.1712.

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2007/75468; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics