Pyrimidines

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. 23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H10N4

II) The control compound DYMDAB was obtained by refluxing an equimolar mixture of 4-dimethylaminobenzaldehyde with 3, 5-dimethyl 2-hydrazino pyrimidine (Scheme 2) in 10 mL methanol for 6 h, leading to light yellow shiny particles, which were filtered, washed with methanol and dried in vacuum.

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Reference:
Article; Makhal, Subhash Chandra; Bhattacharyya, Arghyadeep; Ghosh, Soumen; Guchhait, Nikhil; Journal of Photochemistry and Photobiology A: Chemistry; vol. 358; (2018); p. 138 – 146;,
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Application of 1753-50-0, 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.1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.54, as common compound, the synthetic route is as follows.

To a stirred solution of compound NX (4.9 g, 18.14 mmol) and 2-chloropyrimidine-5-carbonitrile (2.5 g, 18.14 mmol) in EtOH (100 mL), DIPEA (9.8 mL, 54.42 mmol) was added and the reaction mixture was stirred at 80 C for 12 h. The progress of the reaction was monitored by TLC and LCMS. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc (200 mL x 3). The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (15-30% EtOAc/hexane) to afford compound NY (5.0 g, 74.0%) as an off-white solid. LC-MS: m/z 374.15 [M+H]+.

Statistics shows that 1753-50-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloropyrimidine-5-carbonitrile.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1207518-63-5, Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, 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, 1207518-63-5, blongs to pyrimidines compound. name: Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Example 44; (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (44.1); To a suspension of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid methyl ester (example 43) (1.0 g, 4.716 mmol) in dichloromethane (60.0 mL) cooled to -780C, is added a solution of DIBAL-H (1.0 M in toluene, 14.15 mL, 14.15 mmol) dropwise. The resulting solution is stirred at -780C for 2 h and then at room temperature until TLC analysis indicates complete consumption of intermediate 43.2 (3 h). The reaction is quenched with aqueous NH4CI and stirred for 10 min. The salts separated are filtered off and the filtrate is washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue is impregnated over silica gel using methanol and the impregnated silica gel is loaded onto a silica gel column. Elution with a solvent gradient of CH2CI2 : MeOH = 90: 10 followed by evaporation of the eluted solvent gives intermediate 44.1 as a brown solid. 1H NMR (400 MHz, CDCI3): delta 12.35 (brs, 1 H), 8.54 (s, 1 H), 7.54 (s, 1 H), 5.01 (t, J = 5.07 Hz, 1 H), 4.75 (d, J = 5.07 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1207518-63-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHEN, Yen-Liang; DURAISWAMY, Jeyaraj; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15637; (2010); A1;,
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Reference of 1224944-77-7 , The common heterocyclic compound, 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.

General procedure: To a solution of 0.25 g (0.92 mmol) of compound 7-3 dihydrochloride salt in 23 mL of DMSO was added 0.19 g (0.86 mmol) of ethyl 6-chloroimidazo[1 ,2-b]pyridazine-3-carboxylate and 0.40 g (6.8 mmol) of KF. The mixture was stirred at 180 C for 2 h and cooled down to rt. It was diluted with 250 mL of water and extracted with 250 mL of ethyl acetate. The combined organic extracts were washed with brine and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by Prep-TLC (ethyl acetate / petroleum ether = 1 :1 ) to afford compound 7-4. LC-MS: m/e = 386 [M+H]+.

The synthetic route of 1224944-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
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Synthetic Route of 1722-12-9 , The common heterocyclic compound, 1722-12-9, name is 2-Chloropyrimidine, molecular formula is C4H3ClN2, 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.

Ice cooled hydriodic acid (Wako Pure Chemical Industries, Ltd.) (14.7 ml, 57%) was added gradually to 3.68 g (32.0 mmoles) of 2-chloropyrimidine (Sigma-Aldrich Corporation), and the reaction mixture was agitated for fifty minutes at 0C. Ice cooled aqueous sodium carbonate solution was added to the reaction solution until the solution was neutral, and aqueous sodium sulfite solution was subsequently added. The product was extracted using diethyl ether, and the organic layer was dried using anhydrous sodium sulfate after it was washed once using a saturated aqueous sodium chloride solution. The solvent was removed, and the pale yellow oil remaining was dissolved in boiling hexane. The solution was left standing to cool, and 3.62 g (17.6 mmoles, 55%) of colorless needle-like crystals (Compound 2) was obtained. The analytical results for Compound 2 obtained (2-iodopyrimidene) are shown below. 1H-NMR (400 MHz, CDCl3, TMS, rt) delta 8.47 (2H, d, J = 4.8 Hz), 7.32 (1H, t, J = 4.9 Hz)

The synthetic route of 1722-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National University Corporation Hokkaido University; EP2395055; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 959236-97-6, 4-Bromo-2-(methylthio)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, Safety of 4-Bromo-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4-Bromo-2-(methylthio)pyrimidine

A suspension of 4-bromo-2-(methylthio)pyrimidine (9 A, 1.18g, 7.35 mmol) , potassium carbonate (37ml, 0.4 M in water), o-tolylboronic acid (1 g, 7.35 mmol) andtetrakis(triphenylphosphine)palladium(0) (425 mg, 0.37 mmol) in DME (40 ml) was degassed for 20 minutes. It was then heated at reflux for 2 hours. The reaction mixture was cooled and filtered through celite. The filtrate was extracted with EtOAc (2 x 30 ml). The organic layer was dried with Na2S04, filtered and concentrated. The crude product was purified by flash column (Rf: 0.3 10%EtOAc/Hexanes). The yield was 98%. MS (m/z) 217 [M+H]+

The synthetic route of 959236-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
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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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., category: pyrimidines

Step 1 : To a stirred solution of mixture of 4-(2,4-difluorophenyl)-1-(3-fluoro-4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-3-methylimidazolidin-2-one (0.2 g, 0.462 mmol, 1 equiv), in 1 ,4-dioxane: water (10 mL: 3 mL) was added 5-bromo-7-methyl-7H- pyrrolo[2,3-d]pyrimidin-4-amine (0.095 g, 0.416 mmol, 0.9 equiv), potassium phosphate (0.196 g, 0.924 mmol, 2 equiv), Pd2(dba)3 (0.021 g, 0.0231 mmol, 0.05 equiv) and tri-tert- butylphosphonium tetrafluoroborate (0.0133 g, 0.0462 mmol, 0.1 equiv) under argon atmosphere, then the mixture was heated to 100C for 6h in a sealed tube. Reaction mixture was monitored by TLC and after consumption of the starting material, the reaction mixture was filtered through celite, dried over Na2S04, and concentrated to obtain the crude product. Crude product was purified by flash column chromatography on silica gel, and the compound was eluted with 2 % MeOH : DCM mobile phase. The pure fractions were evaporated to obtain 1-(4-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-3- fluorophenyl)-4-(2,4-difluorophenyl)-3-methylimidazolidin-2-one as off white solid (0.07 g, 34.5 %). LCMS (ES) m/z = 453.1 [M+H]+. H NMR (400 MHz, DMSO-d6) delta ppm 2.62 (s, 3H), 3.68 – 3.69 (m, 1 H), 3.71 (s, 3H), 4.28 (t, J = 9.6 Hz, 1 H), 4.97 – 5.01 (m, 1 H), 5.93 (br. S., 2H), 7.15 (t, J = 6.4 Hz, 1 H), 7.24 (s, 1 H), 7.32 (t, J = 8.8 Hz, 2H), 7.40 – 7.49 (m, 2H), 7.69 (d, J = 13.2 Hz, 1 H), 8.1 1 (s, 1 H).

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Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (247 pag.)WO2017/46737; (2017); A1;,
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Reference of 15846-15-8, 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.15846-15-8, name is 4,6-Dimethoxypyrimidin-5-amine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.

EXAMPLE 143 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-(4,6dimethoxypyrimidin-5-ylamino)propanoic acid 5-Amino-4,6-Dimethoxypyrimidine gave the title compound (0.9 mg) HPLC-MS Retention time 2.43 min; MH+ 492.

Statistics shows that 15846-15-8 is playing an increasingly important role. we look forward to future research findings about 4,6-Dimethoxypyrimidin-5-amine.

Reference:
Patent; Celltech Therapeutics Limited; US6348463; (2002); B1;,
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Pyrimidine – Wikipedia

Reference of 2972-52-3, 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 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride. This compound has unique chemical properties. The synthetic route is as follows.

100 g of 2,4-dichloro-5-pyrimidinyl chloride is dissolved in 800 g of anhydrous chloroform,Add 95 grams of triethylamine, lower the temperature to 0 C, and add 38 grams of tert-butylamine dropwise.After the addition, the reaction was held at 0 C for 1 hour.100 g of compound 2,4-dichloro-5-pyrimidine tert-butyramide was obtained by filtration,The measured purity is greater than 98% and the yield is 85%;

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 2972-52-3, 2,4-Dichloro-5-pyrimidinecarbonyl chloride.

Reference:
Patent; Nanjing Puruida Pharmaceutical Technology Co., Ltd.; Wang Xiaobo; (7 pag.)CN110452179; (2019); A;,
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Pyrimidine – Wikipedia

Application of 1193-21-1, Adding some certain compound to certain chemical reactions, such as: 1193-21-1, name is 4,6-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 1193-21-1.

First, 5.0 g of 4,6-dichloropyrimidine,4.9 g of phenylboronic acid, 7.1 g of sodium carbonate, 0.34 g of bis (triphenylphosphine) palladium (II) dichloride (abbreviation: PdCl 2 (PPh) 2) 20 mL of acetonitrile,20 mL of water was placed in a 100 mL round bottom flask provided with a reflux tube, The inside of the flask was replaced with argon. Thereafter, microwave (2.45 GHz, 100 W) was irradiated for 1 hour and heated. The organic layer was extracted from the resulting mixture by dichloromethane,The organic layer was washed with water,Washed with saturated brine,Magnesium sulfate was added and dried. The mixture was naturally filtered. The solvent of the filtrate was removed by distillation,The residue thus obtained was subjected to solid-By purification by flash column chromatography using dichloromethane as a developing solvent,1.6 g of the desired product (yield: 23%, pale yellow solid) was obtained.

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Handotai Energy Kenkyusho Corporation; Inoue, Hideko; Kanamoto, Mickey; Seo, Hiromi; Takahashi, Tsuyoshi; Seo, Satoshi; (43 pag.)KR2015/2504; (2015); A;,
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