Heterocyclic Building Blocks-Tetrahydropyrans

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.

Cesium carbonate (33.6 mmol), 3-amino-5-bromo-1H-pyrazole-4-carbonitrile (22.4 mmol) and bromocyclopentane (2.64 mL, 24.6 mmol) in MeCN (170 mL) was stirred at 80 C for 19 h, then cooled to RT and partitioned between water and EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification gave the titled compound (1.00g, 3.92 mmol, 18% yield). UPLC-MS(ES, Short acidic): 1.58 mi mlz 256.9 [M+2], 25637-16-5

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

Reference£º
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); 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

To 75 g (0.75 mol) of tetrahydropyran-4-one in THF (150 mL) is added a suspension of 28.4 g (0.75 mol) LiAlH4 in THF (600 mL) under nitrogen atmosphere maintaining the temperature below 30 C. with the aid of an ice-bath. Then the reaction is allowed to warm to RT and stirred for 5 h. The reaction is quenched by addition of sat. aq. NH4Cl solution until effervescence ceased. The resulting precipitate is removed by filtration through Celite and washed with THF (150 mL). The filtrate is concentrated under reduced pressure to afford 71.1 g of tetrahydropyran-4-ol. Yield: 92%.

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
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 tetrahydro-2H-pyran-4-ol (U-1 ) (1.02 g, 10 mmol) and Et3N (1 mL) in dried DCM (20 mL) was added MsCI (2 mL) dropwise. The reaction was stirred at room temperature for 1 h, then washed with water. The organic layer was separated, dried over Na2S04, and concentrated to afford the title compound (1.8 g)., 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; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

[01477] To a stirred solution of methyl 3-bromo-4,6-dichloropyridine-2-carboxylate (600 mg, 2. ] mmol) in DMF (5ml) was added TEA (587 mu, 4.21 mmol) followed by N-methyloxan-4- amine (240 mg, 2.1 mmol) and the reaction mixture was heated at 80C for 20h. The reaction mixture was then cooled to room temperature and poured onto water ( 100ml), followed by extraction of the product into EtOAc (3x 100ml), washing of the combined organics with brine (50ml), drying with Na2S04 and evaporation. The crude product was then purified over a l Og silica Isolute column eluting with a gradient of 0% to 100% EtOAc in heptane to afford the title compound as a white solid (1 10 mg, 14%). LC-MS 100%, 1 .94 min (3.5 minute LC-MS method), m/z= 362.8/365.2/346.8, NMR (250 MHz, Chloroform-d) delta 6.87 (s, 1 H), 4.17 – 3.99 (m, 2H), 3.98 (s, 3H), 3.93 – 3.70 (m, 1 H), 3.41 (t, J = 1 0.9 Hz, 2H), 2.81 (s, 3H), 1 .93 (dd, J = 1 1 .9, 4.6 Hz, 2H), 1 .71 (d, J = 10.3Hz, 2H).

220641-87-2, The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To sodium hydride (23.8 mmol) in THF (80 ml) at [0C] was added trimethyl phosphonoacetate (22.86 mmol). The reaction mixture was stirred for 15 minutes and a solution [OF EXAMPLEL] (A) (20.6 mmol) in THF (20 ml) was added. After 20 hours at ambient temperature the reaction was quenched by addition of an aqueous ammonium chloride solution. Extraction with ethyl acetate, drying (sodium sulfate) and evaporation yielded the crude product. Purification by flash column chromatography (silica gel) eluting with ethyl acetate-hexane (1: 5) gave the desired product., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Signal Pharmaceuticals, Inc.; WO2003/105774; (2003); A2;,
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

Example 1384-[4-(2-methoxyphenyl)piperazin- I -yl]-1 -(tetrahydro-2H-pyran-4-yl)- I Hpyrazolo[ 3, 4-d]pyrimidine To 100 mg (0.32 mmo[) 4-[4-(2-methoxypheny[)piperazin-1 -y[]-1 H-pyrazo[o[3,4- d]pyrimidine, 525mg (1.61 mmo[) cesium carbonate and 12.3 mg (0.08 mmo[) sodium iodide in 4 mL anhydrous DMF were added 160 mg (0.97 mmo[) 4-bromotetrahydro- 2H-pyran. It was stirred over night at rt and then 4 h at 50CC. The mixture was concentrated on a rotavap. 20 mL water and 15 mL dich[oromethane were added.The [ayers were separated and the aqueous phase was extracted three times with dich[oromethane. The combined organic phases were washed with brine, dried over magnesium su[fate and concentrated. The residue was purified by HPLC yie[ding 44 mg (34%) product.LC-MS (ana[ytica[ method 3): R = 1.14 mm, MS (ESipos): mlz = 395 (M+H).1H-NMR (300MHz, DMSO-d6): 6 [ppm]= 1.76 – 1.87 (m, 2H), 2.05 – 2.22 (m, 2H), 3.05 -3.14 (m, 4H), 3.47 – 3.60 (m, 2H), 3.82 (5, 3H), 3.94 – 4.03 (m, 2H), 4.03 – 4.11 (m,4H), 4.85 -4.99 (m, 1H), 6.84- 7.03 (m, 4H), 8.28 (5, 1H), 8.33 – 8.38 (m, 1H)., 25637-16-5

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

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; GOLZ, Stefan; TELSER, Joachim; REHWINKEL, Hartmut; SIEBENEICHER, Holger; BUCHMANN, Bernd; ZORN, Ludwig; EIS, Knut; KOPPITZ, Marcus; LINDNER, Niels; HEROULT, Melanie; NEUHAUS, Roland; WO2013/182612; (2013); 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.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.

Step I, i-(4-hydroxy2,2,6,64etrameihyItetrahydro4Hpyran-4y1)eihanone: To astirred solution of ethoyethene (184 g, 25.5 mmol) in THE (40 mE) was added t8J (16rnL, 25.6 mmoi) at -78 C. The reaction mixture was slowly allowed to warm to 10 Cfollowed by addition of 2 ,2,6,6-tetramethyldihydro-2H–pyran-4(3 [1)-one (2 g, 1 2.8 mmol).The mixture was stirred for 16 h at room temperature. The reaction was quenched by theaddition of HCI (3 mL) in aqueous methanol (20 mL, MeOR 1:1). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide the crude title compound as an off-white sob ci (1 .2 g) which was used in the next step without further purification., 1197-66-6

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

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BAKTHAVATCHALAM, Rajagopal; AHMAD, Ishtiyaque; BATTULA, Sivaramakrishna; GIJSEN, Henricus Jacobus Maria; VADIVELU, Saravanan; WALL, Mark; WO2015/23289; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

A mixture of 63 mg (0.15 mmol) E-4, 17 mg (0.15 mmol) methyl-(tetrahydro-pyran-4-yl)-amine, 500 muL NMP and 1 mL dioxane is stirred at 90C for 1 h. The reaction mixture is purified with RP chromatography (C18, 10-80% acetonitrile in water containing 0.1% formic acid). Yield: 12 mg (16%). HPLC-MS: M+H = 514; tR = 0 min.

220641-87-2, 220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (2013); 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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

Reference Example 2: Tetrahydropyran-4-carbaldehyde. To a solution of tetrahydro pyran-4-carbonitrile (1.0 g, 9.0 mmol) in toluene (10 mL) was added diisobutylaluminium hydride solution (DIBAL-H, 10.8 mL, 10.8 mrnol,10 IM in toluene) at -78C. The reaction was stirred at -780C for 1 hour then allowed to warm to r.t. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford tetrahydropyran-4-carb aldehyde (530 mg, 52 %)., 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F2G LTD; WO2008/62182; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 50 mL round bottomed flask, 2,2-dimethyldihydro-2/-/-pyran-4(3/7)-one (0.3 g, 2.3 mmol) was dissolved in water (15 mL) along with sodium metabisulfite (0.22 g, 1.17 mmol). The mixture was allowed to stir at rt for 1 h and N1-benzyl-N1-isopentyl-N2-methylethane-1,2-diamine dihydrochloride (0.72 g, 2.3 mmol) and DIPEA (1.6 mL, 9.4 mmol) were added. The mixture was stirred for 2 h and potassium cyanide (0.243 g, 3.7 mmol) was added to the reaction mixture. The reaction was stirred at rt until full conversion was achieved (12 days). The colourless solution was extracted with ethyl acetate and the combined organic phases were washed with NaHCC>3, dried over MgSC>4, filtered and concentrated to dryness to give the title compound as yellow oil (0.65 g, yield 75%). 1H NMR (400 MHz, CDCl3) delta ppm: 7.41 – 7.13 (m, 5H), 3.83 – 3.77 (m, 2H), 3.58 (s, 2H), 2.61 – 2.41 (m, 4H), 2.23 (s, 3H), 2.02 – 1.93 (m, 2H), 1.69 – 1.51 (m, 5H), 1.49 – 1.39 (m, 2H), 1.38 (s, 3H), 1.23 (s, 3H), 0.86 (d, J = 6.6 Hz, 6H)

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; ALMANSA-ROSALES, Carmen; GARCIA-LOPEZ, Monica; RODRIGUEZ ESCRICH, Sergio; (158 pag.)WO2018/153546; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics