Tag: M.W:100-200

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

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of ethyl 4-chloro-6-(6-(methoxymethyl)pyridin-3-yl)quinoline-3- carboxylate (2 g, 5.61 mmol) and (5)-tetrahydro-2H-pyran-3-amine hydrochloride (0.926 g, 6.73 mmol) in DMF (10 ml) was added DIPEA (3.5 ml, 20.04 mmol) and the solution stirred at 80C for three h then allowed to cool. The reaction mixture was stirred with water (100 ml) and the solid was filtered off, washed thoroughly with water and sucked dry. The crude product was purified by FCC, elution gradient 0 to 3% 2N methanolic ammonia in DCM and pure fractions were evaporated to dryness to afford (5)-ethyl 6-(6-(methoxymethyl)pyridin-3-yl)-4- ((tetrahydro-2H-pyran-3-yl)amino)quinoline-3-carboxylate (1.640 g, 69.4 %) as a white solid. NMR Spectrum: 1H NMR (500MHz, DMSO-d6) 5 1.36 (3H, t), 1.47 – 1.64 (1H, m), 1.67 – 1.94 (2H, m), 1.96 – 2.2 (1H, m), 3.40 (3H, s), 3.56 (1H, dd), 3.61 (2H, t), 3.87 (1H, dd), 4.22 (1H, dd), 4.36 (2H, q), 4.56 (2H, s), 7.54 (1H, dd), 7.95 (1H, d), 8.10 (1H, dd), 8.19 (1H, dd), 8.40 (1H, d), 8.91 (1H, s), 8.92 – 8.93 (1H, m), 8.94 (1H, dd). Mass Spectrum: m/z (ES+)[M+H]+ = 422., 1245724-46-2

1245724-46-2 (S)-Tetrahydro-2H-pyran-3-amine hydrochloride 60145922, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; BARLAAM, Bernard, Christophe; PIKE, Kurt, Gordon; HUNT, Thomas, Anthony; (110 pag.)WO2017/153578; (2017); A1;,
Tetrahydropyran – Wikipedia
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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 L RBF under light nitrogen flow was charged with 2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one (1.00 equiv; 49.10 mL; 43.45 g), (a known compound which may be prepared as described in, for example, MAGNUS, P., et al., ?Synthesis of the ABCD-rings of the insecticidal indole alkaloid nodulisporic acid?, Tet. Lett., 1999, pp 6909-6912, Vol. 40) 2-methyl-THF (375.00 mL; 322.05 g) and DBU (76.67 mL; 77.67 g). The resulting mixture was stirred and cooled to about 2 C. with a water-ice bath. NfsulphF (1.20 equiv; 56.07 mL; 94.20 g) was introduced into a dropping funnel and the NfsulphF was then added to the reaction mixture over 20 minutes, with a light exotherm is observed. After complete addition, the water-ice bath was taken away and the temperature allowed to rise to room temperature. Precipitation was observed to start forming, resulting in a yellow suspension. The yellow suspension was stirred overnight at room temperature and yielded yield a brown suspension. [0249] To the brown suspension was slowly added water (1.12 L; 1.12 kg), with an observed exotherm. The resulting mixture was warmed 44 C., resulting in a multi-phase mixture with good separation (the organic layer was the top layer). The mixture was stirred for 20 minutes and the phases warm separated at about 44 C. The aqueous (orange colored) layer was returned to the RBF, and then extracted with 2-methyl-THF (185.00 mL; 158.88 g) by stirring 20 minutes at 44 C., then warm separating the resulting layers. The organic layers were then combined. Water (190.00 mL; 190.00 g) was added and the resulting mixture stir for 20 minutes, and the resulting layers warm separated at 44 C. The organic layer was then washed second time with water (190.00 mL; 190.00 g), with some white fluffy precipitation observed in the water layer. The organic layer was then evaporated on a rotavap at 45 C. The resulting biphasic residue included a thick brown bottom layer (129.17 g) and light colored material on top. To the residue was added HEPTANE 50% (a mixture of 50% n-heptane, 20% other heptane isomers and 30% methyl cyclohexane; 250.00 mL; 176.75 g), then acetonitrile (19.00 mL; 14.88 g). The resulting mixture was stirred firmly, the acetonitrile was observed to take up the oily layer, resulting in a biphasic system. The mixture was then stirred for 1 hour, the layers separated. The heptane layer was evaporated on a rotovap at 42 C. to yield the title compound as a residue (102.60 g) [0250] Actual Yield: 93.52% 102.60 g, 234.08 mmol [0251] Theoretical Yield: 100% 109.58 g, 250.00 mmol, 1197-66-6

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

Reference£º
Patent; Janssen Pharmaceutica NV; KOLODZIEJCZYK, Krzysztof; Stappers, Alfred Elisabeth; Teleha, Christopher A.; Weerts, Koen Johan Herman; US2014/45789; (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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To an ice-cooled solution of oxan-4-ol (1.00 g, 9.79 mmol), Et3N (1.36 ml, 9.79 mmol) and catalytic amount DMAP in 20 ml of CH2Cl2 was added dropwise MsCl (0.76 ml, 9.79 mmol). The resulting mixture was stirred for 1 h and diluted with water. The mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was pure enough for use in the next step (1.65 g, 93.5 % yield).

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
Article; Zhang, Dengyou; Ai, Jing; Liang, Zhongjie; Li, Chunpu; Peng, Xia; Ji, Yinchun; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5169 – 5180;,
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.

4-Chlorotetrahydropyran (650 muL, 6.0 mmol) was dissolved in THF (6 mL). Magnesium turnings (2.0 g, 80.7 mmol) was added to the mixture followed by methyl iodide (14 muL, 230 mumol). The mixture was stirred at 30 C. for 10 minutes and additional 4-chlorotetrahydropyran (9.3 g, 77 mmol) diluted in THF (60 mL) was added dropwise. 2.0M Isopropylmagnesium chloride in THF (2.0 mL) was added and the mixture was stirred overnight at 30 C. The mixture was cooled to room temperature to give a grey slurry of 0.8M 4-tetrahydropyranmagnesium chloride in THF., 1768-64-5

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

Reference£º
Patent; STANGELAND, Eric; SCHMIDT, Jane; SAITO, Daisuke Roland; HUGHES, Adam; PATTERSON, Lori Jean; US2011/21597; (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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

Step A: Preparation of tetrahydro-2H-pyran-4-yl methanesulfonate: To a solution of tetrahydro-2H-pyran-4-ol (2.5 g, 24.5 mmol) in DCM (40 mL) was added DIEA (6.40 mL, 36.7 mmol) at 0 C and allowed to stir under nitrogen for 10 minutes. Methane sulfonyl chloride (2.18 mL, 28.1 mmol) was added slowly. The reaction was allowed to proceed for 1 hour at 0 C. The reaction was partitioned between 100 mL of DCM and 50 mL of 0.5 M hydrochloric acid. The layers were separated and the organic layer was then washed sequentially with water, saturated sodium bicarbonate, and brine. The organic layer was dried over MgSO t, filtered, and concentrated under reduced pressure and dried on high vacuum to afford tetrahydro-2H-pyran-4-yl methanesulfonate (4.4 g, 24.4 mmol, 99.7% yield).

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

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BURGESS, Laurence, E.; GRONEBERG, Robert, D.; HARVEY, Darren, M.; HUANG, Lily; KERCHER, Timothy; KRASER, Christopher, F.; LAIRD, Ellen; TARLTON, Eugene; ZHAO, Qian; WO2011/130146; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(3-Chloropropyl)-tetrahydro-2H-pyran-4-carbonitrile. To a stirred solution of 1 M LiHMDS (25 mL, 25 mmol) in THF (10 mL) at -78 C. was added dropwise a solution of tetrahydro-2H-pyran-4-carbonitrile (2.23 g, 20 mmol) in THF (15 mL) over 10 minutes. After 40 min, 1-chloro-3-iodopropane (2.7 mL, 25 mmol) was added at once, stirred at -78 C. for 1 h and 4 h room temperature. Then the reaction mixture was diluted with ether (100 mL), washed with water (20 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated to give yellow oil which was purified by flash column chromatography using 10-30% EtOAc/Hexanes to afford the title compound as a colorless liquid (3.74 g, 99%). 1H NMR (500 MHz, CDCl3) delta: 3.97 (2H, dd, J=11.3, 3.7 Hz), 3.71 (2H, td, J=12.2, 1.8 Hz), 3.61 (2H, t, J=6.3 Hz), 2.05-1.98 (2H, m), 1.88 (2H, dd, J=13.4, 1.8 Hz), 1.77-1.74 (2H, m), 1.65-1.59 (2H, m)., 4295-99-2

The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/4265; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Tetrahydropyran-4-one (7.5 g, 75 mmol, 1 equiv.) in MeOH (75 mL) was cooled to 0 C. NaBH4 (1.425 g, 37.5 mmol, 0.5 equiv.) was added in portions at 0 C. The mixture was heated to RT and stirred for 1 h at RT. MeOH was distilled off and the mixture was diluted with iced water, neutralised with acetic acid, and extracted with EA (3¡Á30 mL). The organic phase was concentrated under reduced pressure and the product was obtained as a colourless oil (4.3 g, 56% yield).

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

Reference£º
Patent; Gruenenthal GmbH; US2012/46301; (2012); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62071-40-3,4-(Tetrahydropyran-4-yl)phenylamine,as a common compound, the synthetic route is as follows.

The mixture of 4,6-dichloronicotinonitrile (440 mg, 2.5 mmol), 4-(tetrahydro-2H-pyran-4-yl)aniline (530 mg, 3.0 mmol), DIEA (0.65 mL, 3.75 mmol) in 20 mL DMF was stirred at 90 C. for overnight to afford a mixture of compounds 139.3 (UV=316 nm) and 139.4 (UV=278 nm). The mixture was concentrated in vacuo and subjected to flash column (0-20% EtOAc in DCM) to isolate the 139.3/139.4 product (870 mg). This product mixture (500 mg, 1.6 mmol) was dissolved in 100 mL MeOH with 9 mL DMSO, and was stirred at RT. To it was added K2CO3 powder (440 mg, 3.2 mmol) and then H2O2 (50 wt %, 3 mL). The mixture was stirred at RT for 2 h. It was diluted with 200 mL EtOAc, filtered through celite and concentrated in vacuo. It was subjected to reverse phase prep HPLC to isolate product 139.5 (UV=278 nm) and product 139.6 (UV=287 nm). Compound 139.5 (50 mg, 0.15 mmol) was dissolved in 2 mL in a sealed tube. To it were added 4-aminotetrahydropyran (76 mg, 0.75 mmol) and DIEA (80 muL, 0.45 mmol). The mixture was stirred at 120 C. for 2 days. It was cooled to RT, treated with 0.2 ml, TFA, and subjected to reverse phase prep HPLC to isolate the title compound (48 mg). MS found for C22H28N4O3 as (M+H)+ 397.3. UV: lambda=258 nm. 1H NMR: (CD3OD) delta 8.11 (1H, s), 7.38 (2H, dt, J=8.0; 1.6 Hz), 7.26 (2H, dt, J=8.0; 2.0 Hz), 6.03 (1H, s), 4.05 (2H, m), 3.93 (2H, m), 3.66 (1H, m), 3.61-3.51 (4H, m), 2.86 (1H, m), 1.98 (2H, m), 1.80 (4H, m), 1.61 (2H, m) ppm., 62071-40-3

As the paragraph descriping shows that 62071-40-3 is playing an increasingly important role.

Reference£º
Patent; Portola Pharmaceuticals, Inc.; US2012/108566; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics