Tag: M.W:200-300

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. 10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine, molecular formula is C10H20N2O2Si2, 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. COA of Formula: C10H20N2O2Si2

A mixture of uracil (6.00 g, 53.53 mmol) and ammonium chloride (0.3 g, 5.60 mmol) in HMDS (15 ml) was refluxed for 10 h with the exclusion of moisture until a clear solution was obtained. The excess of silylating agent was removed under vacuum. The residual clear oil of 2,4-bis(trimethylsilyloxy)pyrimidine was dissolved in 25 ml of anhydrous 1,2-dichloroethane, and ethyl bromoacetate (5.92 ml, 53.53 mmol) was added. The reaction mixture was heated at reflux for 20 h, cooled to room temperature and treated with 15 ml of iPrOH. The resulting precipitate was collected and purified by flash chromatography eluting with 1:10 EtOH/1,2-dichloroethane to give 13 (9.45 g, 92%) as white crystals, mp 118-120 C, Rf 0.42 (EtOAc); 1H NMR (400 MHz, DMSO-d6) delta ppm 1.21 (3H, t, J = 7.1 Hz, CH3), 4.15 (2H, q, J = 7.1 Hz, CH2), 4.51 (2H, s, NCH2), 5.62 (1H, d, J = 7.8 Hz, H-5), 7.62 (1H, d, J = 7.8 Hz, H-6), 11.40 (1H, br s, H-3); 13C NMR (100 MHz, DMSO-d6) delta ppm 14.0, 39.1, 39.3, 39.5, 39.7, 39.9, 48.6, 61.2, 101.1, 145.9, 151.0, 163.8, 168.2.

With the rapid development of chemical substances, we look forward to future research findings about 10457-14-4.

Reference:
Article; Babkov, Denis A.; Valuev-Elliston, Vladimir T.; Paramonova, Maria P.; Ozerov, Alexander A.; Ivanov, Alexander V.; Chizhov, Alexander O.; Khandazhinskaya, Anastasia L.; Kochetkov, Sergey N.; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Seley-Radtke, Katherine L.; Novikov, Mikhail S.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1069 – 1081;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 883231-23-0, 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.883231-23-0, name is N-Boc-2-Amino-5-bromopyrimidine, molecular formula is C9H12BrN3O2, molecular weight is 274.11, as common compound, the synthetic route is as follows.

A mixture of tert-butyl (5-bromopyrimidin-2-yl) carbamate (17a) (360 mg, 0.96 mmol) , N, N-dimethylpiperidin-4-amine (246 mg, 1.92 mmol) , Pd2 (dba) 3 (44 mg, 0.048 mmol) , Xantphos (56 mg, 0.096 mmol) , t-BuONa (184 mg, 1.92 mmol) in toluene (11 mL) was heated at 110 for 18 h under N2. The mixture was cooled to room temperature and concentrated in vacco. The residue was purified by chromatography on silica gel eluting with DCM /MeOH (10: 1) to give tert-butyl (5- (4- (dimethylamino) piperidin-1-yl) pyrimidin-2-yl) carbamate (17b) . MS-ESI (m/z) : 322 [M + 1] +.

The chemical industry reduces the impact on the environment during synthesis 883231-23-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHONGQING FOCHON PHARMACEUTICAL CO., LTD.; SHANGHAI FOCHON PHARMACEUTICAL CO., LTD.; ZHAO, Xingdong; LI, Tongshuang; ZHANG, Huajie; LI, Zhifu; LIU, Bin; LIU, Qihong; TAN, Rui; RONG, Yue; YANG, Lijun; CHEN, Zhifang; TAN, Haohan; JIANG, Lihua; LIU, Yanxin; LINGHU, Li; LIN, Min; SUN, Jing; WANG, Weibo; (89 pag.)WO2017/114351; (2017); A1;,
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Related Products of 926663-00-5, 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.926663-00-5, name is Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O3, molecular weight is 207.19, as common compound, the synthetic route is as follows.

The 5-hydroxy pyrazole [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (20.8g), tetrahydrofuran (223 ml) and ethanol (111 ml) is added in the mixture 2M of aqueous sodium hydroxide solution (201 ml). In the reaction mixture is 50 C stirring overnight, and the evaporation of the organic solvent under reduced pressure. Adding the aid hemostasis 2M hydrochloric acid (201 ml), will precipitate and collect the solid by filtration, but also to water/ethanol cleaning and generates a title compound (17.7g).

Statistics shows that 926663-00-5 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; TAKED A PHARMACEUTICAL COMPANY LIMITED; KAWASAKI, MASANORI; MIKAMI, SATOSHI; NAKAMURA, SHINJI; NEGORO, NOBUYUKI; IKEDA, SHUHEI; ASHIZAWA, TOMOKO; MARUI, SHOGO; TANIGUCHI, TAKAHIKO; (135 pag.)TW2016/520; (2016); A;,
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Pyrimidine – Wikipedia

Electric Literature of 38696-20-7, 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.38696-20-7, name is 5-Bromo-2-phenylpyrimidine, molecular formula is C10H7BrN2, molecular weight is 235.08, as common compound, the synthetic route is as follows.

Oxazole (124 mg, 1.8 mmol) was dissolved in stirring tetrahydrofuran (20 mL) under nitrogen at -78° C. and treated with n-butyllithium (2.0 M in cyclohexane, 1.1 mL, 2.2 mmol) maintaining internal temperature below -60° C. After stirring ten minutes, ZnCl2 (0.48 g, 3.5 mmol) was added portionwise. The cooling bath was removed and the solution was allowed to reach room temperature. Tetrakis(triphenylphosphine)palladium(0) (30 mg, 5 mole percent) and 5-bromo-2-phenylpyrimidine (309 mg, 1.30 mmol) were added and the mixture heated at 60° C. for four hours. Solvent was removed under reduced pressure and the mixture partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic phase was retained and additional ethyl acetate extractions of the aqueous phase performed. The combined extracts were dried with anhydrous sodium sulfate, the solution filtered, and solvent removed under reduced pressure. Purification by silica gel flash chromatography (9:1 to 7:3 v/v hexane-ethyl acetate) through a 12-g Silicycle.(R). flash silica cartridge afforded the title compound as an off-white solid (17 mg, 6percent yield); Rf 0.66 with 3:1 v/v hexane-ethyl acetate; melting point 175-177° C.; 1H-NMR (300 MHz; DMSO-d6) delta 9.42 (s, 2H), 8.48 (dd, 2H), 8.41 (s, 1H), 7.56-7.62 (m, 3H), 7.54 (s, 1H); MS (ESI+) m/z 224 (M+1), (ESI-) m/z 222 (M-1); H-PGDS FPBA IC50: 7.8 muM.

The chemical industry reduces the impact on the environment during synthesis 38696-20-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CAYMAN CHEMICAL COMPANY; US2010/75990; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 26032-72-4, 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 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To the reaction flask were added 2,4-dichloro-6-phenylpyrimidine (0.30 g, 1.30 mmol), potassium carbonate (0.37 g, 2.70 mmol), (R)-methyl 3-amino-4,4-dimethylpentanoate (0.46 g,1.70 mmol) and DMF (10 mL).The mixture was stirred at 80 C for 24 h. Water (40 mL) was added, and the resulting mixture was extracted with EtOAc (30 mL x 3). The combined organic phases were washed with saturated brine (60 mL), dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 15/1) to give the tilte compound as a white solid (120 mg, 26 %).MS (ESI, pos. ion) m/z: 348.1[M+H].

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 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1060816-58-1, 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 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl trans-A-((5 -bromo-2-(butylamino)- 7H-pyrrolo[2,3-d]pyrimidin-7-yl methyl)cyclohexylcarbamate A 10 mL microwave tube was charged with 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.23 g, 1.0 mmol), tert-butyl trans-4-(iodomethyl)cyclohexylcarbamate (0.51 g, 1.5 mmol), K2CO3 (0.28 g, 2.0 mmol), DMSO (1.5 mL) and THF (3 mL). The mixture was heated at 150 C for 100 min in microwave. After the reaction mixture was cooled to ambient temperature, n-butylamine ( 0.18 g, 2.5 mmol) was added. The mixture was heated at 150 C for 90 min in microwave. After cooling to ambient temperature, the reaction was poured into water and extracted with EtOAc (3X). The combined organic layer was dried (Na2SO4) and concentrated. The crude mixture was purified by Isco to provide tert-butyl trans-4-((5-bromo-2-(butylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)cyclohexylcarbamate (0.35 g, 73%) as a white solid. MS m/z 480.2 [M+H

According to the analysis of related databases, 1060816-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; LIU, Jing; YANG, Chao; ZHANG, Weihe; FRYE, Stephen; KIREEV, Dmitri; WO2013/52417; (2013); A1;,
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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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Safety of 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

4-methyl-3-((7-((2-(trimethylsilyl)ethoxy)m yl)oxy)benzoic acid: 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3- d]pyrimidine (284 mg, 1.0 mmol), 3-hydroxy-4-methylbenzoic acid (152 mg, 1.0 mmol) and K2C03 (414 mg, 3.0 mmol) were combined in DMSO (5 mL) and stirred overnight at 100 C. The reaction mixture was then cooled to room temperature. The mixture was acidified with IN HQ solution and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography to yield 296 mg of product as a colorless oil. MS (ESI) m/z 400 (M+H)+.

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, 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; TREON, Steven, P.; BUHRLAGE, Sara, Jean; GRAY, Nathanael; TAN, Li; YANG, Guang; WO2015/89479; (2015); A1;,
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.32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, molecular weight is 237.88, as common compound, the synthetic route is as follows.Application In Synthesis of 2,5-Dibromopyrimidine

General procedure: A solution of (1-(3-(difluoromethyl)-4-fluorophenyl)-1 H-i ,2,3-triazol-4- yl)methanol (Intermediate 9, 110 mg, 0.41 mmol), Cs2CO3 (535.9 mg, 1.64 mmol), and i-(2-chloropyrimidin-5-yl)ethan-i-one (83.6 mg, 0.53 mmol) in ACN (0.02 mL) was heated at 110 C overnight. The reaction mixture wascooled, diluted with EtOAc, and washed with sat. aq. NH4CI. The organic layer was dried (Na2504), filtered, and concentrated under reduced pressure. Purification (FCC, 5i02, 0-50% EtOAc in hexanes) afforded the title compound (12 mg, 8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-37-6, 2,5-Dibromopyrimidine, and friends who are interested can also refer to it.

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

Adding a certain compound to certain chemical reactions, such as: 39876-88-5, 4-Chlorobenzofuro[3,2-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, 39876-88-5, blongs to pyrimidines compound. Formula: C10H5ClN2O

Synthesis Example 2 Synthesis of 4Pcczbfpm First, 0.15 g (3.6 mmol) of sodium hydride (60%) was put into a three-neck flask the air in which was replaced with nitrogen, and 10 mL of N,N-dimethylformamide (abbreviation: DMF) was dropped thereinto while stirring was performed. The container was cooled down to 0 C., a mixed solution of 1.1 g (2.7 mmol) of 9-phenyl-3,3′-bi-9H-carbazole and 15 mL of DMF was dropped thereinto, and stirring was performed at room temperature for 30 minutes. Then, the container was cooled down to 0 C., a mixed solution of 0.50 g (2.4 mmol) of 4-chloro[1]benzofuro[3,2-d]pyrimidine and 15 mL of DMF was added, and stirring was performed at room temperature for 20 hours. The resulting reaction solution was put into ice water and toluene was added to the mixture. An organic layer was extracted from the resulting mixture with the use of ethyl acetate and washed with saturated brine. Magnesium sulfate was added and filtration was performed. The solvent of the obtained filtrate was distilled oil and purification was conducted by silica gel colunm chromatography (developing solvent: toluene, and then a mixed solvent of toluene:ethyl acetate=1 :20). Recrystallization using a mixed solvent of toluene and hexane was performed, so that 1.0 g of 4PCCz8fpm, which was the target substance, was obtained as a yellowish white solid in a yield of 72%. Then, 1.0 g of the yellowish white solid was purified using a train sublimation method. In the purification by sublimation, the yellowish white solid was heated at 270 C. to 280 C. with the pressure set at 2.6 Pa and the argon gas flow rate set at 5 mE/mm After the purification by sublimation, 0.7 g of a yellowish white solid, which was the target substance, was obtained at a collection rate of 69%. The synthesis scheme of this step is shown in(A-2) below. Analysis results by nuclear magnetic resonance (?H-NMR) spectroscopy of the yellowish white solid obtained in the above step are described below. These results reveal that 4PCCz8fpm was obtained. ?H-NMR oe(CDC13): 7.31-7.34 (m, 1H), 7.43-7.46 (m, 3H), 7.48-7.54 (m, 3H), 7.57-7.60 (t, 1H), 7.62-7.66 (m, 4H), 7.70 (d, 1H), 7.74-7.77 (dt, 1H), 7.80 (dd, 1H), 7.85 (dd, 1H), 7.88-7.93 (m, 2H), 8.25 (d, 2H), 8.37 (d, 1H), 8.45 (ds, 1H), 8.49 (ds, 1H), 9.30 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39876-88-5, its application will become more common.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Seo, Satoshi; WATABE, Takeyoshi; MITSUMORI, Satomi; (178 pag.)US2017/92890; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1211443-61-6, Adding some certain compound to certain chemical reactions, such as: 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide,molecular formula is C14H17ClN4O, 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 1211443-61-6.

General procedure: tert-butyl (3-((4aminophenyl)sulfonamido)propyl)carbamate (4a, 560mg, 1.70mmol),2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (6,497mg, 1.70mmol),Pd(OAc)2 (30mg, 0.1equiv), BINAP (63mg, 0.06equiv), Cs2CO3(1.11g, 3.40mmol) were dissolved in 1,4-dioxane and degassed with argon for 5 min.The resulted mixture was heated to 105 C for 7 h. After monitored by TLC toobserve completion of reaction, the reaction mixture was filtered through Celite aftercooling to 25 C, then the solvents were removed in vacuo. The crude product waspurified by silica gel column chromatography to afford intermediates 7a in 42% yieldaswhite solid.

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xin; Yu, Chenhua; Wang, Cheng; Ma, Yakun; Wang, Tianqi; Li, Yao; Huang, Zhi; Zhou, Manqian; Sun, Peiqing; Zheng, Jianyu; Yang, Shengyong; Fan, Yan; Xiang, Rong; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia