Day: November 17, 2020

591-55-9 , The common heterocyclic compound, 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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 solution of X-Phos (0.04 equiv) and Pd2(dba)3 (0.02 equiv) in toluene (15 vol) was bubbled with nitrogen and heated to 60 C for 15 min. (2S,4R)-1-(2-(3-Acetyl-5-bromo-1H-indol-1-yl)acetyl)-4-fluoro-N-phenethylpyrrolidine-2-carboxamide(1.2 equiv) and sodium tert-butoxide (1.4 equiv) was added to the reaction mixture and the reaction mixture was heated to 100 C for 16 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give (2S,4R)-l-(2-(3- acetyl-5-(pyrimidin-5-ylamino)-lH-indol-l-yl)acetyl)-4-fluoro-N-phenethylpyrrolidine-2- carboxamide. NMR (400 MHz, DMSO-ifc) delta 8.56 (s, 1H), 8.49 – 8.47 (m, 3H), 8.23 (s, 1H), 8.19 – 8.12 (m, 1H), 8.01 (s, 1H), 7.43 (d, J = 8.8 Hz, 1H), 7.27 – 7.09 (m, 5H), 5.50 – 5.31 (m, 2H), 5.15 (d, J= 17.2 Hz, 1H), 4.35 – 4.31 (m, 1H), 4.19 – 3.85 (m, 2H), 3.56 – 3.40 (m, 1H), 3.24 – 3.13 (m, 1H), 2.72 – 2.66 (m, 2H), 2.41 (s, 3H), 2.41 – 2.33 (m, 1H), 2.01 – 1.98 (m, 1H).

According to the analysis of related databases, 591-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

113583-35-0, 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 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(S)-methyl 2-hydrtoxy-3-methylbutanoate 2.62g (0.02 mol) and 4,6-dimethoxypyrimidine-2-yl methyl sulfone 4.36g (0.02 mol) were dissolved in DMF 100 ml, and K2CO3 3.3 g (1.2 eq) was added thereto. Then, the temperature was maintained at 95C while the mixture was stirred over night. The reacted solution was added to water 100 ml, extracted with diethyl ether, dried with MgSO4, and distilled under reduced pressure to obtain residue. Through purification with silica gel column chromatography, a colorless solid material 3.51g (65%) was obtained: 1H NMR (CDCl3); 1.01 (d, 6H), 2.97 (m, 1H), 3.67 (s, 3H), 3.73 (s, 6H), 4.51 (d, 1H), 6.13 (s, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; SNU R&DB Foundation; Korea Research Institute Of Chemical Technology; EP2497768; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]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, 90213-66-4, blongs to pyrimidines compound. 90213-66-4

In a flask 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.0 g, 5.3 mmol) in DMF (30 rnL) was added NaH (60% in mineral oil, 0.21 g, 5.3 mmol). After stirring 5 min at room temperature the reaction mixture was added tosyl chloride (1.0 g, 5.3 mmol) and stirred 1 h at room temperature. The reaction mixture was diluted with H2O (100 mL) and filtered. The filtered solid was washed with H2O (20 mL) and dried 5 h under house vacuum at 80 0C to afford the title compound as a yellow solid (1.6 g, 90%). 1H NMR (500 MHz, DMSO-d6): delta 2.38 (s, 3H), 6.98 (d, J = 4.1 Hz, IH), 7.50 (d, J = 8.3 Hz, 2H), 8.03 (d, J = 8.5 Hz, 2H), 8.11 (d, J = 4.1 Hz, IH) MS (ES+): m/z 343 (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,90213-66-4, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

113583-35-0, 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 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: For the synthesis of 6-22 to 6-33, intermediate 5 (4.0 mmol),intermediate 2 or 3 (2.66 mmol) and tetrabutyl ammonium bromide(0.3 mmol) were added to 50 mL 90% ethanol. After that the reaction continued for 15 h under reflux and every 2 h the pH value of the mixture was adjusted to >7 by adding saturated sodium bicarbonate solution. The crude product was further extracted three times by using sodium hydroxide solution and ethyl acetate.The aqueous layer was then adjusted by hydrochloric acid to a pH value of 3-4. The product was extracted by ethyl acetate and finally purified by flash column chromatography using dichloromethane/methanol (80:1) and the yields were in the range of 14%-35%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Article; Wu, Ren-Jun; Zhou, Kai-Xuan; Yang, Haijin; Song, Guo-Qing; Li, Yong-Hong; Fu, Jia-Xin; Zhang, Xiao; Yu, Shu-Jing; Wang, Li-Zhong; Xiong, Li-Xia; Niu, Cong-Wei; Song, Fu-Hang; Yang, Haitao; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 472 – 484;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

932-52-5, A common compound: 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione,molecular formula is C4H5N3O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Equipped with a stirrer, thermometer, reflux condenser, the reaction vessel was added 1-amino-phthalide (2) 0.23mol, 5- aminouracil 0.28 mol, stannous chloride 0.31mol, 75% mass fraction cyclohexyl 230ml dioxane, stirred at 170 rpm and speed control, batches of 35% mass fraction of 0.13 mol sodium sulfite solution, the reaction was stirred 7H, filtered, and the filtrate was concentrated under reduced pressure the cyclohexane distilled off, added 630ml of 15% mass fraction of KCl , the precipitated solid was filtered, washed with sodium bromide solution, dried over anhydrous magnesium sulfate, was added to a mass fraction of 80% acetonitrile, and the solution temperature rises to 65 , 80min after filtration, the mass fraction of 95% nitromethane recrystallized to give crystals of 1- phthalide 5-amino-uracil 53.63g, yield 89%.

With the rapid development of chemical substances, we look forward to future research findings about 932-52-5.

Reference:
Patent; Chengdu Chester Technology Co., Ltd.; Peng, Fei; (5 pag.)CN105481837; (2016); A;,
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. 1722-12-9, name is 2-Chloropyrimidine. A new synthetic method of this compound is introduced below., 1722-12-9

2-t-Butyl-4-(1-piperazinyl)-6-trifluoromethylpyrimidine (3) A solution of 60 g (0.25 mol) of the chloropyrimidine described above in 200 ml of ethanol was added dropwise to a boiling solution of 129 g (1.5 mol) of piperazine in 500 ml of ethanol over the course of 2 h, and then the mixture was boiled for a further 6 h. After the reaction was complete, the solvent was removed under reduced pressure, and the residue was mixed with 2 l of water. The product crystallized on cooling and was then filtered off with suction. Yield: 56 g (77% of theory) C13H19ClF3N4 (MW 288) m.p. 78-80 C. 1H-NMR (250 MHZ, CDCl3): d=1.3 (s, 9H); 1.8 (s, 1H); 3.0 (m, 4H); 4.7 (m, 4H); 6.6 (s, 1H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1722-12-9, 2-Chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hoger, Thomas; Starck, Dorothea; Treiber, Hans-Jorg; Schaefer, Bernd; Koser, Stefan; Thyes, Marco; Blank, Stefan; US2002/143179; (2002); 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. 698-29-3, name is 4-Amino-2-methylpyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., 698-29-3

EXAMPLE 5 4-Amino-2-methyl-5-pyrimidinecarboxamidoxime A solution of hydroxylamine base, prepared from hydroxylamine hydrochloride (7.296 g., 0.105 mole) and potassium t-butoxide (11.783 g., 0.105 mole) in dimethyl sulfoxide (200 ml.) in a manner similar to that of Example 1, is allowed to react with 4-amino-2-methyl-5-pyrimidine carbonitrile (13.414 g., 0.100 mole). After addition of dimethyl sulfoxide (50 ml.), the mixture is heated at 40+-1 C. for 92 hours. The solid which separates is collected by filtration, successively washed with methanol (1*50 ml.) and water (3*50 ml.) then dried at 110/0.1 mm. The yield of colorless crystals melting at 263 C. dec. (uncorr.) is 10.059 g. (60.2%). A second crop is obtained by concentrating the combined filtrates in vacuo to give a white solid. This material is washed with water, dried at 110 C./0.1 mm. The yield of colorless crystals melting at 256 C. dec. (uncorr.) is 6.300 g. (37.6%). The total yield of crude product is 16.359 g. (97.8%). The combined fractions are recrystallized from 2-methoxyethanol (Darco G-60) affording 7.887 g. (47.2%) of colorless prisms melting at 264 C. dec. (uncorr.). Concentration of the mother liquors yields a second crop of colorless prisms melting at 265 C. dec. (uncorr.) in a yield of 6.258 g. (37.4%) total yield is 14.145 g. (84.6%). Analysis for: C6 H9 N5 O; Calculated: C, 43.11; H, 5.42; N, 41.90; Found: C, 43.04; H, 5.35; N, 42.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,698-29-3, 4-Amino-2-methylpyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US4323681; (1982); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

171887-03-9 , The common heterocyclic compound, 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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.

To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1 -carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55C for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SC>4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, 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, 56-09-7, blongs to pyrimidines compound. 56-09-7

General procedure: Typically, 2-aminopyrimidine-4,6-diol (1a, 0.5 mmol, 1.0 equiv)/2-methylpyrimidine-4,6-diol (1b, 0.5 mmol, 1.0 equiv), nitroolefins (2, 0.5 mmol, 1.0 equiv), as well as water (2.5 mL) were introduced into a 10 mL reaction vial. Then, the reaction vial was closed and stirred for given time at 90 C. Upon completion, the reaction mixture was cooled to room temperature and diluted with cold water (30 mL). The solid product was collected by filtration and was purified by recrystallization from hot 95% EtOH to afford the goal product 5-arylfuro[2,3-d]pyrimidin-4-ol (3) as off-white to yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56-09-7, its application will become more common.

Reference:
Article; Li, Chunmei; Zhang, Furen; Tetrahedron Letters; vol. 58; 16; (2017); p. 1572 – 1575;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding some certain compound to certain chemical reactions, such as: 271-80-7, name is 1H-Pyrazolo[3,4-d]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 271-80-7. 271-80-7

Compound 8a1 (1 g, 8.33 mmol) was dispersed in 1,2-dichloroethane, and N-iodosuccinimide (2.3 g, 9.02 mmol) and TDA-1 (0.5 ml). The mixture was refluxed at 90 C. After 3 h, the solvent was evaporated and the residue was extracted with hot water. The solid residue was dissolved in ethyl acetate and purified with flash chromatography. The product was obtained as yellowish solid. (1.9 g, 92.7 %). Rf (dichloromethane/MeOH 20:1) 0.34. 1H NMR (400 MHz, DMSO-d6): delta 9.04 (s, 1 H, C6-H), 9.08 (s, 1 H, C2-H), 14.51 (s, 1 H, NH). 13C NMR (101 MHz, DMSO-d6): delta 93.80, 118.55, 153.30, 154.73, 156.52.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 271-80-7.

Reference:
Article; Zhu, Junfei; Li, Zhiwen; Wang, Qi; Liu, Yang; He, Junlin; Bioorganic and Medicinal Chemistry Letters; vol. 26; 18; (2016); p. 4462 – 4465;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia