Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a mixed solution of 62 (7.25 g, 32.5 mmol) and L12CUCI4 (16.2 mL, 0.1 M solution in THF, 1.62 mmol, 5 mol %) in THF (50 mL) at 0C was slowly added Grignard reagent ((cyclobutylmethyl)magnesium bromide) that5 was made from (bromomethyl)cyclobutane (9.69 g, 65.0 mmol) and grinded magnesium turnings (3.16 g, 130 mmol) in Et20 (50 mL). After the addition completed, stirred at 0C for 30 min and then at RT for 18 hr. The reaction was quenched by NH4Cl at 0C and stirred at RT for 20 min. Then the mixture was treated with hexanes and water. Organic phase was washed by brine, dried over Na2S04, and concentrated to give 63 (6.9 g, 100%) as a colorless oil. ‘H NMR (400 MHz, Chloroform-ri) d 4.57 (dd, J= 4.5, 2.7 Hz, 1H), 3.87 (ddd, .7= 11.1, 7.4, 3.4 Hz, 1H), 3.72 (dt, J = 9.6, 6.9 Hz, 1H), 3.56 – 3.45 (m, 1H), 3.37 (dt, J= 9.6, 6.7 Hz, 1H), 2.24 (dq, J= 15.5, 7.8 Hz, 1H), 2.10 – 1.93 (m,3H), 1.91 – 1.64 (m, 4H), 1.62 – 1.45 (m, 7H), 1.39 (q, J= 7.4 Hz, 2H), 1.25 (tdd, J= 10.0, 7.2, 3.9 Hz, 2H). 13C NMR (101 MHz, Chloroform-ri) d 98.78, 67.65, 62.28,36.79, 36.06, 30.73, 29.70, 28.32 (2C), 25.46, 23.77, 19.66, 18.43.

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TSRL, INC.; LIPKA, Elke D.; SIMON, Eric; WHITE, Andy, D.; HUTCHINGS, Kim, M.; GAN, Xinmin; (0 pag.)WO2020/6050; (2020); 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

1240390-36-6, Step 2 {(3R,4R)-4-[7-(5-Methyl-4,5-dihydro-pyridin-2-yl)-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 (5-methyl-4,5-dihydro-pyridin-2-yl)-amide (0.071 g, 0.233 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.0756 g, 0.350 mmol) in dioxane (3 mL) was added diisopropylethylamine (0.122 mL, 0.699 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 Na2SO4, filtered and concentrated. Purification by chromatography (silica, 40 g, 0 to 50% ethyl acetate in hexanes) gave {(3R,4R)-4-[7-(5-methyl-4,5-dihydro-pyridin-2-yl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.047 g, 0.097 mmol, 41.6%) as a yellow solid. LCMS m/z [M+H]=485.

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

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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1172623-99-2, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ruthenium chloride (45 mg) was added to a solution oftert-butyl[(2R,3S)-5-hydroxy-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (15.0 g; Formula IX;Example 10) and acetic acid (15.0 mL) in acetonitrile (45.0 mL) and water (7.5 mL) at0C. Sodium bromate (4.0 g) was added slowly to the reaction mixture at 0C to 5C overS hours, and then the mixture was stirred for 16 hours at -5C to 5C. After completion ofthe reaction, IPA (15 mL) was added over 25 minutes at 0C to 5C, and then the mixture was stirred for 15 minutes. Water (180 mL) was slowly added to the reaction mixture, and then the mixture was stirred for 5 hours at 0C to 5C. The reaction mixture was filtered, and then dried under reduced pressure at 45C to 50C to obtain the title compound.Yield: 80%, 1172623-99-2

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; PANDYA, Bhargav; THAKUR, Mandeep; SURADKAR, Swapnil; ANGADI, Surender; (42 pag.)WO2017/81590; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A. 2,2,6,6-Tetramethyl-tetrahydro-2H-pyran-4-ol, 10a (0297) (0298) A solution of 2,2,6,6-tetramethyloxan-4-one (190 mg, 1.22 mmol) and NaBH4 (93 mg, 2.5 mmol) in THF (4 mL) and methanol (2 mL) was stirred for 1 h at RT. The reaction was then quenched by the addition of 0.1 mL of water. The resulting mixture was concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether (1:5-1:3 v/v)) to give the compound 10a. 1H-NMR (300 MHz, CDCl3) delta (ppm): 3.88-3.97 (m, 1H), 1.71-1.77 (m, 2H), 1.36-1.37 (m, 1H), 1.20-1.25 (m, 1H), 0.97-1.05 (m, 6H), 0.89-0.95 (m, 6H)., 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Huang, Hui; Player, Mark R.; (53 pag.)US2016/9662; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

To a suspension ofguanidine hydrochloride (906 mg, 9.48 mmol) in ethanol (30 mL) was added sodium ethoxide (4.03 mL, 9.48 mmol) and the resulting mixture was stirred at room temperature for 10 mm before addition of methyl 4-oxotetrahydro-2H-pyran-3- carboxylate (1 .00 g, 6.32 mmol) in ethanol (35 mL). The reaction mixture was heatedat 80 00 overnight then concentrated to dryness, the residue was diluted with water and the pH was adjusted to 4 with HCI (iN, aq.). The resulting mixture was stirred at room temperature for 2 hours. The precipitated solids were isolated by filtration, washed with water and dried in vacuo to give the titled compound as a light yellow solid (860 mg, 81%).1H NMR (400 MHz, DMSO-d6) 6 ppm 2.36 (t, J = 5.56 Hz, 2 H),3.77 (t, J = 5.56 Hz, 2 H), 4.24 (s, 2 H), 6.34 (s, 2 H), 10.78 (s, 1 H)., 127956-11-0

As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; GUILLEMONT, Jerome, Emile, Georges; MC GOWAN, David, Craig; EMBRECHTS, Werner, Constant, Johan; COOYMANS, Ludwig, Paul; CALMUS, Laurent; (18 pag.)WO2018/2319; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.141095-78-5,2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: Caution alpha-Azido ketones are potentially explosive compounds and should be handled with care. A mixture of alpha-bromo ketone 1a-g (1 equiv) and sodium azide (1.1-1.2 equiv) in MeOH or Me2CO (2.5 ml/mmol) was stirred for 2-17 h and then the solvent was evaporated. The residue was partitioned between water and EtOAc, the organic layer was washed with water, brine, dried over Na2SO4,and evaporated. alpha-Azido ketones 2d,15 2e,16 and 2f17 have been previously reported in literature. alpha-Azido ketones 2a-c, g do not ionize under ESI LCMS mode conditions and are too unstable to obtain elemental analysis., 141095-78-5

141095-78-5 2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone 13197225, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Bobi?eva, Olga; Lo?a, Ein?rs; Chemistry of Heterocyclic Compounds; vol. 54; 11; (2018); p. 1070 – 1074; Khim. Geterotsikl. Soedin.; vol. 54; 11; (2018); p. 1070 – 1074,5;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

General procedure: In the following Reaction Scheme A-2 Butyl 4-hydroxypiperidine-1-carboxylate (1 eq.) Or tetrahydro-2H-p yr-4-ol (1 eq.),Methanesulfonyl chloride (MsCl, 1 eq.),Triethylamine (Et3N, 1 eq.) And 4-dimethylaminopyridine (DMAP, 0.4 eq.) Were dissolved in dichloromethane at 0 C and stirred at room temperature for 12 hours.Water was added to the reaction solution at 0 C and extracted three times with dichloromethane.The combined organic solvent layers were dried with magnesium sulfate and concentrated.This was purified by column chromatography to obtain a compound substituted with methanesulfonate.Subsequently, 4-iodo-1H-pyrazole (1 eq.) Was dissolved in DMF, cooled to 0 C, 60% sodium hydride (NaH, 1.2 eq.) Was added to the solution and the mixture was stirred at room temperature for 1 hour.The previously obtained compound (1.1 eq) was added to the reaction solution, and the mixture was heated and stirred at 100 C.Water was added to the reaction solution at 0 C, extracted three times with ethyl acetate, and the combined organic solvent layer was dried over magnesium sulfate.The obtained organic solvent layer was concentrated and purified by column chromatography to obtain an intermediate.

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Institute for Basic Science; KAIST; Hong Seung-u; Ma Sin-mi; Hong Sun-seon; Jeong Hoe-yun; (71 pag.)KR2019/23557; (2019); A;,
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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.

1H (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 mixture and allowed to react to room temperature for 4 hours. Cool down to 0 C,Saturated sodium hydrogen carbonate solution (60 mL) was added dropwise to the reaction mixture, stirred for 20 minutes, and filtered.The filtrate was allowed to stand for stratification, and the aqueous phase was extracted with methyl tert-butyl ether (60 mL ¡Á 3).Wash with saturated sodium bicarbonate solution (30 mL ¡Á 2), dry over anhydrous sodium sulfate, and then concentrated by filtration and eluted by column chromatography ( petroleum ether / ethyl acetate (v/v) = 10:1-4:1 ),The white crystalline powder Intermediate 1 (10.85 g, yield 94.7%) was obtained., 1172623-99-2

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Feng Jianchuan; Peng Fei; Chen Qingping; (45 pag.)CN105085530; (2019); B;,
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137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 294.1. (E)-3-(Dimethylamino)-l-(tetrahydro-2H-pyran-4-yl)prop-2- en-l-one. To a sealed tube were added l-(tetrahydro-2H-pyran-4-yl)ethanone (3.00 g, 23.4 mmol) and DMF-DMA (6.2 mL, 46.8 mmol). The reaction mixture was heated at 100 C overnight. The resulting mixture was concentrated under reduced pressure to afford 4.00 g (crude) of the title compound as light yellow oil.

137052-08-5, As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Tetrahydropyran – Wikipedia
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29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 221,1-Dimethylethyl 2-(tetrah dro-2H-pyran-4-yl)hydrazinecarboxylateTetrahydro-4H-pyran-4-one (9.69 g, 97 mmol) was added to a solution of 1,1- dimethylethyl hydrazinecarboxylate (14.07 g, 106 mmol) in methanol (100 mL) and stirred at room temperature for 3 h. The solvent was removed in vacuo, and the crude residue was suspended in acetic acid (140 mL). Next added sodium cyanoborohydride (6.69 g, 106 mmol) in portions over 3 minutes. The contents were stirred at room temperature for 60 h. The solvent was removed in vacuo, and the crude residue was suspended in DCM (100 mL). The reaction mixture was adjusted to pH 7 with 6N NaOH. The layers were separated, and the aq. layer extracted with DCM. The combined organic layers were washed with saturated NaHC03, and brine. The organic layer was dried over MgS04, filtered, and concentrated in vacuo to afford the product as a solid, 18.4 g (88%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.22 (m, 2 H), 1.39 (s, 9 H), 1.43 – 1.48 (m, 1 H), 1.59 – 1.69 (m, 2 H), 2.82 – 2.98 (m, 1 H), 3.20 – 3.32 (m, 2 H), 3.80 (d, J=l 1.62 Hz, 2 H), 4.36 (br. s., 1 H), 8.07 – 8.34 (m, 1 H)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics