Pyrimidines

Synthetic Route of 22536-61-4, 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

A 40 mL pressure vial was charged with Example 29.4 (71 mg, 0.16 mmol) which was then dissolved in DMSO (1.6 mL). To that solution was added 2-chloro-5-methylpyrimidine (83 muL, 0.80 mmol) followed by Hunig’s base (277 muL, 1.59 mmol). The vial was sealed and placed into a reaction block preheated to 100 ¡ãC. After 4 h, the reaction was cooled to RT and diluted with DCM and water. The contents of the vial were transferred into a separatory funnel and the layers were separated. The organic layer was washed with water (x3). The aqueous layer was analyzed for product and showed a large presence of product. The aqueous layer was re-extracted using 3:1 EtOAc/EtOH (x3). The combined organic layers were dried with magnesium sulfate, filtered and concentrated under reduced and purified by flash chromatography: Redi-Sep Rf Gold 12g – CV = 16.8mL, eluting with EtOAc:EtOH 3:1 (v/v) in DCM 0percent (2 CV), 0-40percent (15 CV), 40percent (5 CV) to provide Example 29.5 (54 mg, 0.10 mmol, 63 percent yield) as an orange solid. LCMS-ESI (pos.) m/z: 538.2 (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,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
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Electric Literature of 165807-05-6 ,Some common heterocyclic compound, 165807-05-6, molecular formula is C7H11N3O2, 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.

Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaHydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48¡ã C. for 16 hr.The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).The organics were combined, dried and then evaporated in vacuo.The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 165807-05-6, 4-Dimethoxymethylpyrimidin-2-ylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1514-96-1, 4-Chloro-2-(trifluoromethyl)pyrimidine, 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, 1514-96-1, blongs to pyrimidines compound. Quality Control of 4-Chloro-2-(trifluoromethyl)pyrimidine

To a solution of (S)-2-amino-4-((3,3-difluoropropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid (140 mg, 328 mumol) in THF (4 mL) and H2O (1 mL) was added 4-chloro-2-(trifluoromethyl)pyrimidine (66 mg, 361 mumol) and NaHCO3 (138 mg, 1.64 mmol) and the resulting mixture was stirred at 70 C. for 18 h and then allowed to cool to rt and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=531.2 (M+H)+. 1H NMR (400 MHz, D2O) delta ppm 8.22 (br d, J=5.75 Hz, 1H) 7.49 (br d, J=7.09 Hz, 1H) 6.84 (d, J=6.24 Hz, 1H) 6.52 (br d, J=7.34 Hz, 1H) 5.91-6.26 (m, 1H) 4.72 (br s, 1H) 3.14-3.50 (m, 8H) 2.61-2.78 (m, 4H) 2.21-2.52 (m, 4H) 1.82-1.94 (m, 2H) 1.69 (br s, 4H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1514-96-1, its application will become more common.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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, Product Details of 3764-01-0, blongs to pyrimidines compound. Product Details of 3764-01-0

Preparation of Compound 1-4 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136,29 mmol), Pd(PPh3)4 (3.15 g, 2.72 mmol), 2M K2CO3 (50 mL), toluen (100 mL) and ethanol (30 mL) were stirred under reflux. 4 hours later, the mixture was cooled to room temperature and extracted with EA after adding distilled water. After drying with MgSO4 and distillation under reduced pressure, Compound 1-4 (7 g, 48.%) was obtained by column separation.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee Choon; KIM, Nam Kyun; CHO, Young Jun; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; WO2011/99718; (2011); A1;,
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Application of 611-08-5, 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. 611-08-5, name is 5-Nitrouracil. A new synthetic method of this compound is introduced below.

General procedure: In a double-necked round-bottom flask (100 mL) wasadded a mixture consisting of nucleobase (0.01 mol),alcohol (0.012 mol), TsCl (2.86 g, 0.015), TEA (1.01 g,0.01 mol) and K2CO3 (1.38 g, 0.010 mol) in bmim[Br](10 mL). The flask was immersed in an oil bath, kept at80 C and stirred for the time when TLC indicated no furtherprogress in the conversion (Tables 4, 5, 6). The mixturewas then diluted with water (200 mL) and extracted withEtOAc (3 ¡Á 50 mL). The organic layer was dried (Na2SO4)and evaporated to afford the crude product which was purifiedby traditional column chromatography on silica geleluting with proper solvents.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Article; Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Zarenezhad, Elham; Kaviani, Narjes; Journal of the Iranian Chemical Society; vol. 12; 9; (2015); p. 1603 – 1612;,
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Adding a certain compound to certain chemical reactions, such as: 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 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, name: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, blongs to pyrimidines compound. name: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.3 g, 9.7 mmol, 1.0 eq) in CHC13 (45 mL) was added NIS (2.18 g, 9.7 mmol, 1.0 eq) at rt. The solution was refluxed for 2 h. The precipitate was filtered and dried in vacuo to give 5-iodo-7H- pyrrolo[2,3-d]pyrimidin-4-ylamine (2.09 g, 83%) as a white solid.

The synthetic route of 1500-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
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Reference of 287714-35-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-(N-Boc-amino)piperidine 9.3 g was added to a 250 mL three-necked flask.N,N-dimethylacetamide 100mL,N,N-diisopropylethylamine 7.5 g,2-chloropyrimidine-5-carboxylic acid methyl ester 4.0 g,Stir at room temperature for 3 h under nitrogen.The end of the reaction was monitored by TLC (petroleum ether: ethyl acetate = 2:1).200 mL of water was added and extracted with dichloromethane (100 mL x 3), and the organic phases were combined.The organic phase was washed successively with 5% dilute hydrochloric acid (100 mL¡Á3) and saturated sodium chloride (100 mL¡Á3).The organic phase was dried over anhydrous sodium sulfate for 2 h, filtered, and evaporated, evaporated, evaporated.A white solid was obtained in 6.8 g, yield: 87.1%.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Radioactive Medical Institute; Li Yiliang; Wei Huiqiang; Gao Jun; Bi Changfen; Ning Hongxin; Yu Jiang; Gou Wenfeng; Duan Yuqing; (35 pag.)CN109232541; (2019); A;,
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Pyrimidine – Wikipedia

Electric Literature of 1209459-32-4, Adding some certain compound to certain chemical reactions, such as: 1209459-32-4, name is 4-(2-Bromopyrimidin-4-yl)morpholine,molecular formula is C8H10BrN3O, 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 1209459-32-4.

To a microwave tube was added N-isopropyl-3-(trimethylstannyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine (200 mg, 0.344 mmol), 4-(2-bromopyrimidin-4-yl)morpholine (168 mg, 0.688 mmol), LiCl (58.0 mg, 1.38 mmol), CuI (13.0 mg, 0.0688 mmol), Pd(PPh3)4 (40.0 mg, 0.0344 mmol), and THF (3.0 mL). After three cycles of vacuum/argon flash, the reaction mixture was heated at 100 C. for 1 hour under microwave irradiation. After cooling down to room temperature, the mixture was filtered via Celite. The filtrate was concentrated under reduced pressure. The residue was purified by prep-TLC eluting with petroleum ether/ethyl acetate (1:2) to afford the title compound as a yellow solid (25 mg, 13%).

According to the analysis of related databases, 1209459-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Estrada, Anthony; Shore, Daniel; Sweeney, Zachary; US2014/288043; (2014); A1;,
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Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 29274-24-6

To 5-chloropyrazolo[l,5-a]pyrimidine (200 mg, 1.31mmol) in 1.5ml DMF was added POCI3 (358 3.92 mmol). The reaction was stirred at room temperature overnight. The mixture was cooled to 0 C in ice bath and the then neutralized with 6M NaOH. The solid formed was isolated by filtration and air dried to give 165 mg of 5-chloropyrazolo[l,5- a]pyrimidine-3-carbaldehyde as yellow solid (70% yield). LCMS (M+l=182)

The synthetic route of 29274-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYLENE PHARMACEUTICALS INC.; HADDACH, Mustapha; RYCKMAN, David; RAFFAELE, Nicholas; WO2011/31979; (2011); A1;,
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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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Dissolve 4-chloro-pyrrolo[2,3-d]pyrimidine (20 mmol) in DMF (6 mL), add NBS or NCS (21 mmol) in portions on ice bath, react at room temperature for 12 h, and pour the reaction mixture into 80 mL of ice. In the water, a large number of off-white solids precipitated and were filtered. The filter cake was washed with 15 mL of water and dried to give Intermediate 2. 4-Chloro-5-bromo-pyrrolo[2,3-d]pyrimidine (2b) Off-white solid, yield 95%

With the rapid development of chemical substances, we look forward to future research findings about 3680-69-1.

Reference:
Patent; Shandong University; Zhao Guisen; Yang Dezhi; Liu Meixia; Zhang Zhen; Zhang Qian; Yang Qingtao; (36 pag.)CN107556318; (2018); A;,
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