Category: Tetrahydropyrans

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.

101691-94-5, Example 10 Synthesis of 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-((tetrahydropyran-4-yl)methoxy)quinazoline (Compound 15) 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-hydroxyquinazoline trifluoroacetic acid salt (400mg, 0.84mmol), 4-iodomethyltetrahydropyran (190mg, 0.84mmol) and potassium carbonate (289mg, 2.09mmol) were dispersed in N,N-dimethylformamide (DMF, 5mL). The mixture was stirred for 15 hours at 60C to conduct the reaction. The resulting reaction mixture was cooled to room temperature and poured into water (100mL). The resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (methylene chloride_methanol=50:1) to produce a white solid (170mg, yield: 44%). 1H-NMR(400 MHz, DMSO-d6) delta: 9.53(s, 1H), 8.35(s, 1H), 7.80(s, 1H), 7.66(dd, 1H, J = 9.8, 2.0 Hz), 7.53(t, 1H, J = 8.4 Hz), 7.47(dd, 1H, J = 8.4, 1.6 Hz), 7.20(s, 1H), 4.02(d, 2H, J = 6.4 Hz), 3.95(s, 3H), 3.89(dd, 2H, J = 11.4, 3.0 Hz), 3.41-3.33(m, 2H), 2.16-2.03(m, 1H), 1.76-1.66(m, 2H), 1.45-1.32(m, 2H). MS 462, 464(M+1).

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

Reference£º
Patent; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; SHI, Ying; GAO, Qingzhi; CHEN, Xiaozhuo; MI, Yi; ZHANG, Yaran; YANG, Hanyu; CHEN, Yujie; LIU, Chunlei; MI, Guorui; MA, Yuxiu; SHEN, Dongmin; GUO, Yang; FAN, Linjing; (59 pag.)EP3181554; (2017); A1;,
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, Example 30. 2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro- pyran-4-yl)-amideStep 1To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3- b]pyrazine-7-carboxylic acid (0.20 g, 0.59 mmol) in CH2C12 (5 mL) was added EDC (0.14 g, 0.72 mmol), 4-(dimethylamino)pyridine (0.088 g, 0.72 mmol), and (4-aminotetrahydropyran- 4-yl) -methanol (0.094 g, 0.72 mmol). The reaction mixture was stirred at room temperature overnight then diluted with H20 and extracted with CH2C12. The combined organics were washed with brine, dried over Na2S04 and concentrated. The residue was purified by Si02 chromatography (60% EtOAc/hexanes) to obtain 0.15 g (57%) of 2-cyclopropyl-5-(2- trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4- hydroxymethyl-tetrahydro-pyran-4-yl)-amide as an oil.

720706-20-7 (4-Amino-4-tetrahydropyranyl)methanol 18316484, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HENDRICKS, Robert Than; HERMANN, Johannes Cornelius; KONDRU, Rama K.; LOU, Yan; LYNCH, Stephen M.; OWENS, Timothy D.; SOTH, Michael; YEE, Calvin Wesley; WO2011/144584; (2011); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

85064-61-5, 2-(6-Fluoro-4-(piperazin-l-yl)quinazolin-2-yl)phenol (25 mg, 0.077 mmol), 2-(tetrahydro-2i7-pyran-4-yl)acetic acid (14.3 mg, 0.10 mmol), triethylamine (22uL, 0.154 mmol),and HATU (38 mg, 0.10 mmol) were stirred in DMF (1 mL) overnight. Purification via reversephase HPLC (10-99percent CH3CN (0.035percent TFA)/H20 (0.05percent TFA)) gave l-(4-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1 -yl)-2-(tetrahydro-2No.-pyran-4-yl)ethanone. LC/MS:m/z 451.5 (M+H)+ at 2.60 min (10percent-99percent CH3CN (0.035percent TFA)/H20 (0.05percent TFA)).

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/28904; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of tert-butyl 5- (6-cyclopropyl-2-oxo- 1 ,2-dthydropyridine-4-carbonyl)-3 ,4,5 ,6-tetrahydropyrrolo [3 ,4-c]pyrrole-2( 1 H)-carboxylate (385 mg, 985 j.imol), potassium carbonate(272 mg, 1.97 mmol) and 4-(iodomethyl)tetrahydro-2H-pyran (459 mg, 1.97 mmol) inacetonitrile (8 mL) was heated at 90C for 48 h, then partitioned between sat. aq. ammoniumchloride solution and ethyl acetate. The organic layer was washed with brine, dried overmagnesium sulfate, filtered and evaporated. The residue was chromatographed (silica gel; gradient dichloromethane to dichloromethane/methanol/25 % aq. ammonia solution 95:5:0.25) to produce the title compound (390 mg, 84%). White foam, MS: 470.3 (M+H).

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DI GIORGIO, Patrick; HERT, Jerome; HUNZIKER, Daniel; MATTEI, Patrizio; RUDOLPH, Markus; SCHMITZ, Petra; ULLMER, Christoph; (88 pag.)WO2017/50791; (2017); A1;,
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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 2 {(3R,4R)-4-[7-(1-Methyl-1H-pyrazol-4-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (1-methyl-1H-pyrazol-4-yl)-amide (0.137 g, 0.349 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.111 g, 0.513 mmol) in dioxane (4 mL) was added diisopropylethylamine (0.244 mL, 1.4 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 15% MeOH in dichloromethane) to give {(3R,4R)-4-[7-(1-methyl-1H-pyrazol-4-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.116 g, 0.244 mmol, 52.6%) as a yellow solid. LCMS m/z [M+H]=474, 1240390-36-6

The synthetic route of 1240390-36-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
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1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c., 1228779-96-1

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Step 3: Synthesis of Compound B4Prepared as described by adaptation of the following literature reference:Watson, RJ. et al. Tetrahedron Lett. 2002, 43, 683-685.To a solution of 224 g (0.83 mol) of compound B3 in methyl isobutylketone (1.6 L) are added 189 g (1.66 mol) of potassium thioacetate. The beige suspension is stirred at 70 C for 4.5 h. The reaction mixture is cooled to room temperature and water (1.8 L) is added. The organic layer is washed with 10% aqueous K2CO3 solution (1.8 L) and water (1 L). The organic layer is filtered through celite (20 g), activated charcoal (20 g) and Na2S04 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n- heptanes (250 mL) to afford 138 g of compound B4 as a yellow-orange oil (CAUTION: Stench.). Yield: 96%; ES-MS: m/z 175 [M+H]; ]H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.23 – 1.40 (2 H, m), 1.59 – 1.78 (3 H, m), 2.33 (3 H, d, 7=4.16 Hz), 2.82 (2 H, dd, 7=6.24, 3.79 Hz), 3.27- 3.39 (2 H, m), 3.88 – 4.02 (2 H, m)

101691-65-0, The synthetic route of 101691-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (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.125995-03-1,Atorvastatin lactone,as a common compound, the synthetic route is as follows.

[R-(R*,R*)]-2-(4-fluorophenyl)-beta , delta -dihydroxy-5-(l-methylethyl )-3- phenyl-4-[(phenylamino)carbonyl]-lH-pyrrole-l-heptanoic acid potassium<68> lOOg of atorvastatin lacton was dissolved to 1 L of acetone and 10.38g of potassium hydroxide dissolved in 100 mL of water was added thereto over 1 hour. The reaction solution was stirred for 8 hours at room temperature, the solvent was completely removed by a distillation under reduced pressure, and the residue was distilled under vacuum, suspended to 500 mL of acetone, and filtered. The filtrate was dried for 24 hours at a temperature of 60 C to obtain 95g pf atorvastatin potassium.

125995-03-1, The synthetic route of 125995-03-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTECH CO., LTD.; WO2009/54682; (2009); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the protected pyrrole 15 (6.0 g, 22.8 mmol) and ammonium chloride (390 mg, 7.3 mmol) in methanol (15 mL) was added magnesium powder (4.4 g, 180 mmol) and the mixture was sonicated for 1 hour. The reaction mixture was slowly quenched with saturated aqueous ammonium chloride (200 mL) and extracted with diethyl ether (3 x 50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude pyrrole was used immediately without further purification or characterisation. To a solution of the pyrrole (2.3 g, 18.7 mmol), (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (6.1g, 22.4 mmol) and tetrabutylammonium bromide (603 mg, 1.9 mmol) in N,N-dimethylformamide (100 mL) at 0 C was added sodium hydride (60% dispersion in mineral oil, 972 mg, 24.3 mmol) and the mixture was immediately warmed to 50 C and stirred for 16 hours. The mixture was cooled to 0 C, quenched with saturated aqueous ammonium chloride (30 mL), diluted with water (200 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were washed with water (3 x 100 mL) and aqueous lithium chloride (1 M, 2 x 50 mL), dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by flash column chromatography using ethyl acetate, hexane (1:9) as an eluent to obtain the title compound (2.2 g, 52%) as an orange oil, Rf: 0.36 (1:9 ethyl acetate, hexane); IR (vmax (film)): 2955, 2863, 2842, 1200, 1093, 770 cm-1; 1H NMR (300 MHz, CDCl3): delta 1.24 (9H, s), 1.21-1.42 (2H, m), 1.42-1.58 (2H, m), 1.82-2.02 (1H, m), 3.36 (2H, td, J = 11.8, 2.1 Hz), 3.68 (2H, d, J = 7.2 Hz), 3.89-4.04 (2H, m), 6.06 (1H, s), 6.39 (1H, s), 6.52 (1H, s) ppm; 13C NMR (75 MHz, CDCl3): delta 30.7, 30.9, 32.0, 37.5, 55.8, 67.7, 105.8, 116.2, 120.6, 135.7 ppm; LRMS (-ESI) m/z: 220.4 ([M-H]- 100%)., 101691-65-0

Big data shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Article; Moir, Michael; Boyd, Rochelle; Gunosewoyo, Hendra; Montgomery, Andrew P.; Connor, Mark; Kassiou, Michael; Tetrahedron Letters; vol. 60; 36; (2019);,
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.

To a solution of [4-(7-Hydroxymethoxyquinazolin-4-yl)piperidin-l-yl][4- (trifluoromethoxy)phenyl]methanone (100 mg, 0.24 mmol) in 1 mL of N,N-dimethyl formamide were added potassium iodide, (41 mg, 0.3 mmol) and 4-(bromomethyl)-tetrahydro-2H-pyran, 119 mg (0.72 mmol). The resulting solution was stirred 12 h at 80C. After chromatography, the title compound was obtained as a brown solid (24 mg, 26%). After filtration, removal of the solvent and susequent chromatography, the product was obtained as a white solid in 10% yields (12 mg). MS (ESIpos): m/z = 502 (M+H)+; LC-MS[Method 2] : R, = 1.52 min; 1H-NMR (400 MHz, DMSO -d6) d 1.63-1.72 (m, 2H), 1.86-1.90 (m, 4H), 2.06-2.09 (m, 2H), 3.07-3.08 (m, 1H), 3.56 (t, 2H), 3.68-3.69 (m, 1H), 3.88 (t, 2H), 3.96-3.99 (m, 1H), 4.61-4.62 (m, 2H), 4.90-4.94 (m, 1H), 7.36 (d, 1H), 7.44-7.46 (m, 3H), 7.59 (d, 2H), 8.38 (d, 1H), 9.09 (s, 1H).

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

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; NGUYEN, Duy; WORTMANN, Lars; FARIA ALVARES DE LEMOS, Adelaide, Clara; BOeMER, Ulf; SUeLZLE, Detlev; HOLTON, Simon; LECHNER, Christian; (147 pag.)WO2019/170543; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics