Heterocyclic Building Blocks-Tetrahydropyrans

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. A solution of 4-chlorotetrahydro-2H-pyran (1 g, 8.29 mmol) in anhydrous THF (8 mL) was added dropwise to a mixture of Mg (401 mg, 16.5 mmol) and I2 (105 mg, 0.414 mmol) in anhydrous THF 2 mL) under N2 at 60oC. The mixture was stirred at 60oC for 10 min. The temperature rose to 66oC. The reaction mixture was stirred for additional 30 min, cooled to room temperature which was used directly as a solution of (tetrahydro-2H-pyran-4-yl)magnesium chloride (0.83 M in THF)., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (2018); 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.

Preparation 27; 4-Bromo-2-((tetrahydro-2H-pyran-3-yl)oxy)pyridine To a solution of tetrahydro-2H-pyran-3-ol (0.10 g, 0.97 mmol) in THF (2.5 mL) was added sodium hydride (60% dispersion in mineral oil, 0.065 g, 1.6 mmol) and stirred at ambient temperature for about 2 h. To the reaction mixture was added 4-bromo-2-fluoropyridine (0.144 g, 0.816 mmol) in THF (2.5 mL). After about 16 h, water (5 mL) and EtOAc (10 mL) were added. The organic layer was separated and the aqueous layer was back extracted with EtOAc (10 mL). The combined organic layers were dried over MgS04, filtered and concentrated under reduced pressure. The material was purified via flash chromatography on silica gel (0-50% EtOAc/heptane). The appropriate fractions were collected and concentrated under reduced pressure to provide the title product (0.1 17 g, 55%); LC/MS (Table A, Method i) = 1.33 min.; MS m/z: 258 and 260 (M+H) ., 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; ABBVIE INC.; ARGIRIADI, Maria; BREINLINGER, Eric; DIETRICH, Justin, D.; FRIEDMAN, Michael; IHLE, David; MORYTKO, Michael; MULLEN, Kelly; OSUMA, Augustine; LO SCHIAVO, Gloria, Y.; WILSON, Noel, S.; (303 pag.)WO2016/168633; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of tetrahydropyran-3-one (0.25g) and 2-amino-2-(4-bromophenyl)acetamide (D1 ) (0.572g) and H-Y Zeolites (0.57g) in methanol (25ml) was refluxed under argon overnight. The mixture was filtered through Kieselguhr and the solvent was removed to give crude title compound as a yellow solid which was used without purification (712mg). Mass spectrum Found 311/3 (MH+)., 23462-75-1

The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/34061; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

General procedure: Sodium hydride (60% suspension in mineral oil, 31 mg, 0,76 mmol) is added to asolution of 36a (109 mg, 91 % content, 0,63 mmol) in DMF (1 mL) at 0C. After 20mi 2-(trimethylsilyl)ethoxymethyl chloride (157 p1, 0,88 mmol) is added dropwise tothe reaction mixture. After stirring for 1 h at rt, the reaction is diluted with EtOAc,washed with NaHCO3 satured solution and brine. The organic layer is separated and dried with a Phase separator cartridge and evaporated under vacuum to give a residue that is purified by flash chromatography (eluent 0-10% EtOAc/cyclohexane) to furnish the title compound (182 mg).UPLC-MS (Method 2): Rt = 1 .61MS (ESI pos): mlz = 288 (M+H)+

25637-16-5, 25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
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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, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

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;,
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Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, Example 570.5 mmol of an anhydride (1m) was dissolved in 10 mL of methyl t-butyl ether at 20 C., 10 mol % of an organocatalyst (Q-BTBSA) was added thereto, 10 equivalents of methanol was added once thereto, and the mixture was stirred at 20 C. for 1 hours. This reaction was quenched using an aqueous solution of dilute hydrochloric acid (1N, 3 mL). The aqueous layer was extracted with ethyl acetate (2¡Á10 mL), and the combined organic layer was dried with MgSO4 and concentrated. The residue was purified by flash chromatography (25% ethyl acetate in normal-hexane) to obtain a hemiester (1 h, 92% yield). According to the known method (H. Han, Tetrahedron Lett. 2004, 45, 3301-3304), it was determined to obtain an enantiomeric excess of 92% by reacting the hemiester and R-1-(1-naphthyl)ethyl amine to be converted to an ester amide corresponding to the hemiester. The enantioselectivity was measured using high performance liquid chromatography (Kromasil, 90.5:9.5, hexane:isopropyl alcohol, 1 mL/min., t (main product)=9.4 min., t (side product)=17.4 min.).1H NMR (300 MHz, CDCl3) delta 2.56-2.78 (m, 4H), 3.55-3.65 (m, 4H), 7.13-7.16 (m, 2H), 7.24-7.27 (m, 2H); 13C NMR (75 MHz, CDCl3) delta 37.25, 40.00, 40.19, 51.70, 128.56, 128.74, 132.71, 140.63, 171.80, 177.22

As the paragraph descriping shows that 53911-68-5 is playing an increasingly important role.

Reference£º
Patent; SUNGKYUNKWAN UNIVERSITY FOUNDATION FOR CORPORATE COLLABORATION; US2011/213151; (2011); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

POC13 (3.1 g, 20.0 mmol, 1 eq) was added dropwise to DMF (1.46 g, 20.0 mmol, 1 eq) over 5 minutes at 0C. Dichloromethane (10mL) was added and then the ice-bath was removed. The reaction was kept at 25C for 1 hour, then it was cooled to 0C again. Dihydro-2H-pyran-3(4H)-one 1-4 (2 g, 20.0 mmol, 1 eq) in 5 mL of dichloromethane was added dropwise within 5 minutes. The reaction was kept at 0C for 1 hour. The reaction mixture was quenched by adding 20 mL of sat. NH4C1, and extracted three times with 30 mL of DCM. The combined organic phases were washed with 20 mL of brine,dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si02 eluting with a gradient of petroleum ether: ethyl acetate = 50:1 to 20:1) to give 470 mg of compound 1-5 as a yellow oil.

23462-75-1, As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); 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.

A mixture of 58 (3g, 16.75mmol) and potassium thioacetate CH3COSK (3.4g, 33.5mmol) in DMF (60mL) was stirred at 90C for 2h. The reaction mixture was poured into cold water and then extracted with ethyl acetate (3¡Á30mL). The combined organic layers were washed with water (3¡Á60mL) and brine (30mL), and then dried over anhydrous MgSO4 and evaporated to dryness. The crude product was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2-5%) to give the title compound 59 as a yellow oil, (1.8g, yield=69%). 1H NMR (400MHz, CDCl3) delta 3.94 (dd, J=11.6Hz, 4.4Hz, 2H), 3.36-3.33 (m, 2H), 2.81 (d, J=6.4Hz, 2H), 2.32 (s, 3H), 1.69-1.65 (m, 3H), 1.30 (qd, J=12.4Hz, 4.0Hz, 2H); LC/MS (ESI, m/z) 175.08 [M+H]+., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0,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.

Example 6Synthesis of tetrahydropyran-4-carboxylic acid amide; In a vessel made of a glass, having an inner volume of 100 ml and equipped with a stirring device, a thermometer and a reflux condenser were charged 6.30 g (38.5 mmol) of tetrahydropyran-4-carboxylic acid chloride synthesized in the same method as in Example 5 and 20 g (329 mmol) of 28% by weight aqueous ammonia, and the mixture was reacted at 0 C. for 6 hours under stirring. After completion of the reaction, the reaction mixture was filtered, and the obtained filtrate was dried to obtain 4.84 g (Isolation yield; 62%) of tetrahydropyran-4-carboxylic acid amide was white crystals.Physical properties of the tetrahydropyran-4-carboxylic acid amide were as follows.1H-NMR (CDCl3, delta (ppm)); 1.46 to 1.62 (4H, m), 2.26 to 2.52 (1H, m), 3.28 to 3.34 (2H, m), 3.81 to 3.87 (2H, m), 6.77 to 7.24 (2H, d)CI-MS (m/e); 130 (M+1)

40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UBE INDUSTRIES, LTD.; US2008/306287; (2008); 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

To a solution of 6 (300 mg, 1.60 mmol) in DMF (3 mL) was added sodium hydride (95 mg, 60% dispersion in mineral oil, 2.38 mmol) and 4-bromo-tetrahydro-2H-pyran (458 mg, 1.75 mmol). The resulting mixture was stirred for 18 h at room temperature. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resultant residue was purified by column chromatography (0-5% gradient of EtOAc in hexane) to provide the title compound (340 mg, 78%) as a colouless oil. 1H NMR (400 MHz, CDCl3) ppm 1.60 – 1.76 (m, 2 H), 1.92 (dd, J = 11.87, 1.52 Hz, 2 H), 3.20 – 3.33 (m, 1 H), 3.39 – 3.51 (m, 2 H), 3.93 – 4.05 (m, 2 H), 7.28 – 7.34 (m, 2 H), 7.42 – 7.49 (m, 2 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
Article; Semple, Graeme; Santora, Vincent J.; Smith, Jeffrey M.; Covel, Jonathan A.; Hayashi, Rena; Gallardo, Charlemagne; Ibarra, Jason B.; Schultz, Jeffrey A.; Park, Douglas M.; Estrada, Scott A.; Hofilena, Brian J.; Smith, Brian M.; Ren, Albert; Suarez, Marissa; Frazer, John; Edwards, Jeffrey E.; Hart, Ryan; Hauser, Erin K.; Lorea, Jodie; Grottick, Andrew J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 71 – 75;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics