Heterocyclic Building Blocks-Tetrahydropyrans

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

d) Synthesis of 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid ethyl ester To a solution of 2-bromo-4-isopropyl-thiazole-5-carboxylic acid ethyl ester (0.50 g, 1.80 mmol) in 1-methyl-2-pyrrolidone (10 ml) are added potassium carbonate (0.37 g, 2.70 mmol) and N-methyltetrahydro-2H-pyran-4-amine (0.62 g, 5.40 mmol) at RT and the reaction mixture is heated at 150 C. for 16 h. After completion of the reaction, the mixture is diluted with methyl tert-butyl ether (20 ml) and washed with water (3*20 ml) and brine (3*20 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid ethyl ester (0.56 g, 1.92 mmol, 99%).

220641-87-2, As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.

Reference£º
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148454; (2014); 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

To the stirred solution of tetrahydro-4H-pyran-4-one (2 g, 9.33 mmol), tert-butoxycarbonyl hydrazide (1.8 g, 13.99 mmol) in AcOH: MeOH (1 :1 , 10 mL), NaCNBH3 (0.52 g, 8.4 mmol) was added portion wise at 0 C and the reaction mixture was stirred at RT for 30 min. Completion of the reaction was monitored by TLC; the reaction mixture was then concentrated under vacuum. The resulting mixture was suspended with 10% NaHC03 (20 mL) and was extracted with DCM (2 x 15 ml_). The combined organic layer was washed with brine (10 mL), dried over anhydrous Na2S04 and concentrated under vacuum to afford the title compound. Yield: 99% (crude) (2 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.20 (s, 1 H), 4.34 (s, 1 H), 3.82-3.81 (m, 2H), 3.29-3.26 (m, 2H), 2.89-2.88 (m, 1 H), 1.63 (t, J = 2.0 Hz, 2H), 1.38 (s, 9H), 1.24 (t, J = 4.0 Hz, 2H). LCMS: (Method A) 1 17.2 (M-Boc), Rt. 1.2 min, 99.7%., 29943-42-8

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

Reference£º
Patent; ASCENEURON S.A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (179 pag.)WO2019/37861; (2019); 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: To a cooled solution of compound 6 (361.0 mg, 1 mmol) in DMF (10 mL) was added NaH (60% in oil, 48.0 mg, 1.2 mmol) carefully. The mixture was stirred at 0 C for 1h. A solution of R1X (X=Cl, Br; 1.2 mmol) in DMF (5 mL) was then added dropwise in the mixture. The mixture was heated to 40 C and stirred for 8-16 h. The reaction mixture was cooled and quenched at 0 C with a saturated NH4Cl aqueous solution. Then mixture was concentrated under vacuum to remove most of the DMF and re-dissolved with CH2Cl2. After filtering, the filtrate was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum. The crude material was purified by column chromatography (PE/EA) on silica gel to afford compound 6a-6r., 25637-16-5

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

Reference£º
Article; Chen, Peng; Zhang, Dianwen; Li, Meng; Wu, Qiong; Lam, Yuko P.Y.; Guo, Yan; Chen, Chen; Bai, Nan; Malhotra, Shipra; Li, Wei; O’Connor, Peter B.; Fu, Hongzheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of NaH (1.8 g, 40 mmol) in anhydrous THF (10 mL) was added reagent 1 (2.0 g, 20 mmol). The mixture was stirred at room temperature for 1 h before addition of a solution of 4-methylbenzene-1 -sulfonyl chloride (4.6 g, 24 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 15 h. The solution was quenched with saturated, aqueous NH4CI solution (30 mL). The mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over Na2S04 and evaporated to dryness. Flash chromatography (silica, petroleum ether : EtOAc 100:1 to 1 :1 ) gave reagent 2 (4.7 g, 92%). 1H NMR (CDCIs) delta 7.79 (d, J = 8.4 Hz, 2 H), 7.33 (d, J = 4.0 Hz, 2 H), 4.64-4.70 (m, 1 H), 3.82-3.87 (m, 2 H), 3.42-3.48 (m, 2 H), 2.43 (s, 3 H) , 1 .75-1.87 (m, 2 H), 1 .68-1.74 (m, 2 H)., 2081-44-9

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

A solution of N-methyl-(tetrahydro-pyran-4-yl)-amine (0.25 g, 2.17 mmol), Cs2CO3 (1.41 g, 4.34 mmol) and compound 4 (0.85 g, 2.17 mmol) in THF (20 mL) is stirred at room temperature for 72 h. The reaction mixture is filtered through Celite , the solids are washed with ethyl acetate and DCM and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent: heptanes, 50-100% ethyl acetate) to yield 374 mg of compound 5. Yield 41%;. LC-MS (LC Method b): retention time: 1.51 min, m/z 424 [M+H], 220641-87-2

As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; HICKEY, Eugene, Richard; RIETHER, Doris; WU, Lifen; ZINDELL, Renee; BLUMIRE, Nigel; ERMANN, Monika; GLENN, Edward, Thomas; KHOR, Someina; ZAWADZKI, Przemyslaw; WO2010/147792; (2010); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-4-ol (612 mg, 6 mmol) in DCM (5 mL) was added EtsN (1002 uL, 7.2 mmol) and MsCI (510 uL, 6.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. After that the mixture wasconcentrated to give a white solid which was used for next step directly.

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; WO2014/86032; (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.61363-56-2,2H-Pyran-3,5(4H,6H)-dione,as a common compound, the synthetic route is as follows.,61363-56-2

EXAMPLE 52 4-(4-chloro-3-nitrophenyl)-1-methyl4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione The product from Example 45A (0.085 g, 0.75 mmol), 3nitro-4-chlorobenzaldehyde(0.14 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol) were heated in 2 mL of ethanol for 2 days. The resulting mixture was allowed to cool to ambient temperature and filtered to provide the title compound as the filter cake (0.09 g). 1H NMR (300 MHz, DMSO-d6) delta 3.28 (s, 3H), 4.06 (s, 2H), 4.58 (s, 2H), 4.88 (s, 1H), 7.6 (dd, 1H), 7.7 (d, 1H), 7.9 (d, 1H), 10.8 (s, 1H); MS (ESI) m/z 376 (M+H)-; Anal. Calcd for C16H12N3ClO6: C, 50.88;H, 3.20; N, 11.12. Found: C, 50.86;H, 3.63; N, 10.52.

The synthetic route of 61363-56-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 10; 6-[Lambda/-(2,4-Difluorophenyl)-Lambda/-(3-hydroxypropyl)amino]-2,2-dimethyl-1, 2,3,4- tetrahydronaphthalen-1 -one; a) 6-[Lambda/-(2,4-Difluorophenyl)-W-(3-(tetrahydropyran-2-yloxy)propyl)amino]- 2,2-dimethy 1-1 ,2,3,4-tetrahydronaphthalen-1 -one; To a suspension of 6-(2,4-difluorophenylamino)-2,2-dimethyl-1 , 2,3,4- tetrahydronaphthalen-1-one (1.94 g, 6.44 mmol, obtained in example 4) in dry toluene (70 mL), sodium hydride (0.56 g, 55% dispersion in oil, 12.83 mmol) and 15-crown-5 (47 mg, 0.21 mmol) were added under argon and the mixture was stirred at room temperature for 20 min. Then, 3-bromopropanol tetrahydropyranyl EPO ether (1.44 g, 6.44 mmol) was added and the mixture was heated at 90 0C for 4 h. It was allowed to cool and diluted with EtOAc and saturated NaHCO3. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated to afford the desired compound (quantitative yield). LC-MS (method 1): tR = 11.98 min; m/z = 444.2 [M+H]+., 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; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); 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.693287-79-5,tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate,as a common compound, the synthetic route is as follows.

Intermediate 31: 1,1-Dimethylethyl 2-(2,5-dichloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate. [Show Image] To a solution of Intermediate 26 (3.6 g, 16.8 mmol) in dry EtOH (60 mL), 2,4,5-trichloropyrimidine (ALDRICH, 3.4 g, 18.5 mmol) and DIPEA (FLUKA, 8.5 mL, 50 mmol) were added and the resulting reaction mixture was refluxed for 3h, then stirred at room temperature for 3 days. In order to drive the reaction to completion the reaction mixture was refluxed for further 7h, then stirred at room temperature for 12 h. The mixture was concentrated under reduced pressure and the residue partitioned between DCM and 1M ammonium chloride. The organic layer was treated with brine and dried over anhydrous MgSO4. The residue was purified by flash chromatography (eluent: Hex/AcOEt mixtures 49:1 to 1:1) to give the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm: 9.80 (s, 1H), 8.28 (s, 1H), 4.75- 4.56 (m, 1H), 3.96- 3.82 (m, 2H), 3.46- 3.31 (m, 2H), 1.82-1.25 (m, 13H)., 693287-79-5

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP; EP1918284; (2008); 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

Cap- 188, step aTo a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2 g, 15.60 mmol) in 50 niL of MeOH was slowly added sodium borohydride (0.649 g, 17.16 mmol). The resulting mixture was stirred at room temperature for 3 hours. To the mixture was then added 1 N HCl aqueous solution until it crosses into acidic pH range and then extracted with EtOAc (3X). The combined organic layers were dried withMgS04 and concentrated to afford Cap-188, step a (1.9 g) as clear oil. The product was used in the next step without purification. XH NMR (400 MHz, CDCI3) delta ppm 3.91 – 4.02 (1 H, m), 3.79 – 3.86 (1 H, m), 3.63 (1 H, td, J=12.05, 2.51 Hz), 1.82 – 1.93 (2 H, m), 1.40 – 1.53 (1 H, m), 1.29 – 1.38 (1 H, m), 1.27 (3 H, s), 1.20 (3 H, s), 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; WO2012/21591; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics