Category: 22536-65-8

Electric Literature of 22536-65-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

A suspension of 4-((4-((benzo[d][1,3]oxathiol-6-yl)-2-fluorophenoxy)methyl)piperidine (155 mg, 0.45 mmol)), 2-chloro-5-methoxypyrimidine (78 mg, 0.54 mmol) and diisopropylethylamine (87 mg, 0.68 mmol) in acetonitrile (10 mL) was stirred at reflux overnight. Upon cooling, the reaction mixture was allowed to cool to ambient temperature and the solvent was removed in vacuo and the crude product was purified by column chromatography eluting with hexanes: ethyl acetate (4: 1) to obtain the title product (63 mg, 31%) as a white powder.

The chemical industry reduces the impact on the environment during synthesis 22536-65-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

To (1 -(3-(difluoromethyl)phenyl)-5-methyl-1 H-i 2,3- triazol-4-yl)methanol (45 mg, 0.19 mmol) stirring in THF (1 mL) was added NaH (60percent dispersion in mineral oil, 22.6 mg, 0.56 mmol) and the reaction wasstirred for 5 mi 2-Chloro-5-methoxypyrimidine was then added and the reaction was stirred at rt for 1 h. The reaction was quenched with H20, then diluted with EtOAc and H20. The layers were separated and the aqueous layer was extracted with EtOAc (3X). The combined organic layers were washed with H20 (ix), brine (ix), then dried (Na2504) and concentratedunder reduced pressure. Purification (FCC, 5i02, EtOAc/hexanes 0 – 60percent)afforded the title compound (41 mg, 62percent). MS (ESI): mass calcd. forC15H15F2N502, 347.1; m/zfound, 348.0 [M+H]. 1H NMR (400 MHz, CDCI3) O8.24 (5, 2H), 7.71 ? 7.56 (m, 4H), 6.73 (t, J = 56.1 Hz, 1 H), 5.56 (5, 2H), 3.88(5, 3H), 2.45 (5, 3H).

The chemical industry reduces the impact on the environment during synthesis 22536-65-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 72 N-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]-6-[5-(methylsulfonyl)-2,3-dihydro-1H-indol-1-yl]-N-(trifluoromethyl)pyrimidin-4-amine; [Show Image] 6-[5-(Methylsulfonyl)-2,3-dihydro-1H-indol-1-yl]-N-(piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine (100 mg, 0.227 mmol) obtained in Reference Example 34 and 2-chloro-5-methoxypyrimidine (131 mg, 0.906 mmol) were dissolved in NMP (5.0 mL). Cesium carbonate (295 mg, 0.906 mmol) was added thereto, and the mixture was stirred at 80°C for 74 hr. After cooling to room temperature, the mixture was diluted with ethyl acetate, and water was added thereto. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:4 (volume ratio)–>hexane:ethyl acetate=2:8 (volume ratio)], and the obtained solid was suspended in diisopropyl ether. The precipitate was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give the title compound (17.8 mg, yield 14percent) as a white solid. 1H-NMR (300 MHz, CDC13) delta:1.90 – 2.03 (m, 2 H), 2.04 – 2.24 (m, 2 H), 2.93 (t, J=12.7 Hz, 2 H), 3.04 (s, 3 H), 3.32 (t, J=8.7 Hz, 2 H), 3.81 (s, 3 H), 4.12 (t, J=8.9 Hz, 2 H), 4.69 – 4.88 (m, 3 H), 6.24 – 6.31 (m, 1 H), 7.73 (d, J=1.1 Hz, 1 H), 7.80 (dd, J=8.7, 1.9 Hz, 1H), 8.10 (s, 2 H), 8.56 (d, J=8.7 Hz, 1 H), 8.62 (d, J=1.1 Hz, 1 H).

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C5H5ClN2O

Prepare 1L four-necked flask with a stirring device and thermometer.Add 100 g of 2-chloro-5-methoxypyrimidine,300 mL of acetic acid was added to the reaction flask,Stir well, then add 153g of 48% hydrobromic acid and 1g of methionine.Warming up to reflux reaction for 5 h,Sampling HPLC controlled until the end of the reaction, product content 96%, dihydroxy by-product 0.5%;After dropping to room temperature, 300 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane.The organic phases were combined and washed with saturated sodium bicarbonate solution.Then, it is dried over anhydrous sodium sulfate, and after filtration, the organic phase is concentrated under reduced pressure to give a crude product;The crude product was recrystallized from the crude product to give a pale yellow solid, 82 g.The yield was 91% and the purity was 98%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; Haimen Ruiyi Pharmaceutical Technology Co., Ltd.; Xue Song; Zhou Wenjun; (5 pag.)CN110041269; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.Recommanded Product: 2-Chloro-5-methoxypyrimidine

General procedure: 0.69 g (3.59 mmol) 5-bromo-2-chloro-pyrimidine and 0.70 g (2.99 mmol) of the amine Xlll.1 are added to 10 mL DMSO and 0.78 mL (4.49 mmol) DIPEA. The mixture is stirred at 35° C over night and afterwards purified by HPLC (MeOH/H20/NH3).C17H19BrN4O2 (M= 391 .3 g/mol)ESI-MS: 391/393 [M+H]+Rt (HPLC): 1 .80 min (method A) The following compounds are prepared analogously to example 3.1 : For the example 3.2 the reaction mixture is stirred for 4 d at 45° C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-65-8, 2-Chloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; ROTH, Gerald Juergen; NOSSE, Bernd; HEINE, Niklas; WO2013/92616; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-65-8, 2-Chloro-5-methoxypyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 22536-65-8, blongs to pyrimidines compound. category: pyrimidines

Prepare 1L four-necked flask with a stirring device and thermometer.Add 100 g of 2-chloro-5-methoxypyrimidine,300 mL of acetic acid was added to the reaction flask,Stir well, then add 153g of 48% hydrobromic acid and 1g of methionine.Warming up to reflux reaction for 5 h,Sampling HPLC controlled until the end of the reaction, product content 96%, dihydroxy by-product 0.5%;After dropping to room temperature, 300 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane.The organic phases were combined and washed with saturated sodium bicarbonate solution.Then, it is dried over anhydrous sodium sulfate, and after filtration, the organic phase is concentrated under reduced pressure to give a crude product;The crude product was recrystallized from the crude product to give a pale yellow solid, 82 g.The yield was 91% and the purity was 98%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-65-8, its application will become more common.

Reference:
Patent; Haimen Ruiyi Pharmaceutical Technology Co., Ltd.; Xue Song; Zhou Wenjun; (5 pag.)CN110041269; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-65-8 , The common heterocyclic compound, 22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A) 5-methoxypyrimidine-2-carbonitrile To a solution of 2-chloro-5-methoxypyrimidine (4.4 g) and 1,4-diazabicyclo[2.2.2]octane (6.7 g) in a mixed solvent of dimethyl sulfoxide (114 mL) and water (18 mL) was added potassium cyanide (4.00 g). The reaction mixture was stirred at 70°C for 5 hr, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.5 g). 1H NMR (400 MHz, CDCl3) delta 4.02 (3H, s), 8.47 (2H, s).

The synthetic route of 22536-65-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 58C (45 mg, 0.124 mmol) was dissolved in Dioxane (621 mu) and 2- chloro-5-methoxypyrimidine (26.9 mg, 0.186 mmol), dicyclohexyl(2′,4′,6′-triisopropyl- 3,6-dimethoxy-[l, l’-biphenyl]-2-yl)phosphine (6.66 mg, 0.012 mmol), sodium tert- butoxide (17.89 mg, 0.186 mmol), and palladium(II) acetate (2.79 mg, 0.012 mmol) were added. Reaction was degassed with nitrogen bubbling/sonication for 5 minutes, then it was sealed at heated to 85 C for 14 hours. The reaction was diluted with water, acidified with 1 N HC1, and extracted with EtOAc. The combined organics were dried with sodium sulfate, filtered and concentrated. The crude residue was dissolved in DMF, filtered, and purified via preparative HPLC to give Racemic Example 63 (2.5 mg, 0.006 mmol, 4.6%). LC-MS Anal. Calc’d for C24H34N4O4 442.26, found [M+H] 443.3. Tr = 1.869 min (Method B). 1H MR (500 MHz, DMSO-d6) delta: 8.62 (s, IH), 8.34 (s, 2H), 8.12 (d, J=2.7 Hz, IH), 7.14 (d, J=8.7 Hz, IH), 6.35 (dd, J=8.5, 2.7 Hz, IH), 4.72 (q, J=6.5 Hz, IH), 3.83 (s, 3H), 1.76-1.91 (m, 2H), 1.67 (d, J=10.9 Hz, 2H), 1.51-1.54 (m, IH), 1.49 (d, J=6.6 Hz, 3H), 1.15 (t, J=7.2 Hz, 9H), 0.81 (br. s., 6H)

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; (203 pag.)WO2016/210414; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 22536-65-8

A mixture of 2-chloro-5-methoxypyrimidine (7 g, 48.4 mmol) and ammonium hydroxide (113 mL, 2905 mmol) was heated at 100 °C in a sealed tube for 18 h. The mixture was cooled to rt and was concentrated. The residue was was purified on silica gel using 40-80 percent ethyl acetate in hexanes. The desired fractions were concentrated to give a pale yellow solid (2.75 g, 45 percent). 1H NMR (400 MHz, CDCl3) d ppm 8.02 (2 H, s), 4.80 (2 H, br. s.), 3.79 (3 H, s). LCMS (method B) tR, 0.81 min., MH+ = 293.3.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Article; Iwuagwu, Christiana; King, Dalton; McDonald, Ivar M.; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Mate, Robert A.; Fang, Haiquan; Knox, Ronald; Gallagher, Lizbeth; Post-Munson Amy Easton, Debra; Miller, Regina; Benitex, Yulia; Siuciak, Judy; Lodge, Nicholas; Zaczek, Robert; Morgan, Daniel; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1261 – 1266;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-65-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 22536-65-8 as follows.

A mixture of 2.1 g (14.5 mmol) 2-chloro-5-methoxypyrimidine, 4.9 g (16.0 mmol) tert- butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1 – carboxylate, 339 mg (0.29 mmol) tetrakis(triphenylphosphine)palladium(0), 14.5 ml (29 mmol) 2M Na2CO3 solution and dioxane is heated to 140°C for 15 min using a microwave reactor. The reaction mixture is cooled to RT and DCM and water are added, the organic phase is separated and evaporated and purified by HPLC. Giving rise to tert-butyl 4-(5-methoxypyrimidin-2-yl)-3,6-dihydro-2H-pyridine-1 -carboxylate.Yield: 3.5 g (83percent), ESI-MS: m/z = 292 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-65-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; BLUM, Andreas; PETERS, Stefan; (80 pag.)WO2017/148518; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia