Pyrimidines

Electric Literature of 75833-38-4, Adding some certain compound to certain chemical reactions, such as: 75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile,molecular formula is C5H2ClN3, 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 75833-38-4.

General procedure: (2S)-N-(1-((3,3-difluorocyclobutyl)carbamoyl)-2,3-dihydro-1H-inden-1-yl)-N- (5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide (100 mg, 0.21 mmol), 2-chloroisonicotinonitrile( 29 mg, 0.21 mmol), Cs2CO3( 137 mg, 0.42 mmol), Pd2(dba)3(19 mg, 0.021 mmol) and Xant-Phos(24 mg, 0.042 mmol) was stirred under N2 at 90oC overnight. After filtration, the filtrate was concentrated in vacuo and the residue was purified by Pre-HPLC(base) to obtain two diastereoisomers as (S)-1-(4-cyanopyridin-2-yl)-N-((S)-1-((3,3-difluorocyclobutyl) carbamoyl)-2,3-dihydro-1H-inden-1-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide (1b, 10 mg, 9% yield) and (S)-1-(4-cyanopyridin-2-yl) -N-((R)-1-((3,3-difluorocyclobutyl) carbamoyl)-2,3-dihydro-1H-inden-1-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2- carboxamide as white solid(1b?, 12 mg10% yield).

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. 75833-38-4, 2-Chloropyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zheng, Qiangang; Tang, Shuai; Fu, Xianlei; Chen, Ziqi; Ye, Yan; Lan, Xiaojing; Jiang, Lei; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5262 – 5266;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-5-nitropyrimidine

Step D: tert-butyl ethyl but-3~yn-1-yl(5-nitropvrimidin-2-yl)propanedioate: A suspension of NaH (60 percent, 2.5 g, 62.4 mmol) in 100 mL ofDMF was added tert-butyl ethyl but-3-yn-1-ylpropanedioate (15 g, 62.4 mmol) drop-wise at 25 oc. The mixture was stirred at 40 oc for 30minutes and 2-chloro-5-nitropyrimidine (10.0 g, 62.4 mmol) in 50 mL ofDMF was addeddropwise. The resulting suspension was stirred at 50 oc for 2 hours and diluted with 500 mL ofEtOAc. The mixture was washed with water (3 x 100 mL), brine, dried over anhydrous Na2S0430 and concentrated. The residue was purified by column chromatography (Petroleum ether :EtOAc = 10 : 1) to afford the title compound; MS m/z 364 (M+ 1)+.

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, 10320-42-0, 2-Chloro-5-nitropyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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Electric Literature of 4316-98-7 ,Some common heterocyclic compound, 4316-98-7, molecular formula is C4H5ClN4, 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.

2D. 6-Chloro-7,9-dihydropurin-8-one; A mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N’-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86%) LC/MS (LCTl): Rt 2.45 [M+H]+ 173, 171.

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. 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75110; (2008); A1;,
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Reference of 31575-35-6, 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. 31575-35-6, name is 2-Fluoropyrimidine. A new synthetic method of this compound is introduced below.

To a stirred solution of 1 -[(2E)-3 -(piperidin-4-yl)prop-2-enoyl] -5 ,6-dihydropyridin-2(111)-one TFA salt (100 mg, 0.29 mmol, 1 eq) in ethanol (5 mL) was added DIPEA (0.22 mL,1.28 1 mmol, 4.4 eq) and 2-fluoropyrimidine ( 45 mg, 0.469 mmol, 1.6 eq) and the reaction mixture was allowed to stir at 100C in microwave for 30 minutes. Progress of reaction was monitored by LCMS and TLC. After completion, reaction mixture was concentrated under reduced pressure to yield crude product which further purified by Combi-Flash on silica gelusing ethyl acetate-hexane as eluent to yield 1- { (2E)-3 -[1 -(pyrimidin-2-yl)piperidin-4-yl]prop-2-enoyl}-5,6-dihydropyridin-2(1I])-one (30 mg, 23 %).LCMS: 313 [M+H]1H NMR (400 MHz, CHC13) 5 8.29 (d, 2 H), 6.92 (m, 3 H), 7.00-6.80 (m, 3H), 6.42 (t, 1H), 6.00(d, 1H), 4.80-4.70 (m, 2H), 3.98 (t, 2H), 3.02-2.88 (m, 2H), 2.60-2.39 (m, 3H), 1.90-1.80 (m,2H), 1.63-1.40 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31575-35-6, 2-Fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
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Electric Literature of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

General procedure: To a solution of 25a (200 mg, 0.458 mmol) in NMP (4 ml)was added 2-chloro-5-(trifluoromethyl)pyrimidine (100 ng,0.549 mmol) and K2CO3 (189 mg, 1.374 mmol) at room temperature.The reaction mixture was heated at 90 C for 3 h. After cooling to room temperature, the reaction mixture was diluted with water.The aqueous layer was separated and then extracted with EtOAc. The combined organic extracts were washed with water and brine,dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel: CHCl3/MeOH = 95/5) to afford 26a

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
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Application of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

Add compound 13 to a 25 mL single-mouth bottle with magnetic stirrer and condenser(160 mg, 0.61 mmol), compound 7 (192 mg, 0.61 mmol)And ethylene glycol monomethyl ether (4mL), stir and dissolve,Add hydrogen chloride isopropanol solution (0.91 mmol, 0.18 mL, 5 M) dropwise.The temperature was raised to 120 C under a nitrogen atmosphere and stirred to react overnight. Cool to room temperature,Add water(10 mL) and saturated sodium bicarbonate (5 mL), dichloromethane (15 mL×3)The organic phase was combined, washed with saturated brine, dried over anhydrous sodiumConcentrated, the residue was passed through a silica gel column to give a white solid200 mg, the yield was 60.7%.

According to the analysis of related databases, 1197953-49-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (49 pag.)CN109851638; (2019); A;,
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Synthetic Route of 353272-15-8, 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. 353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Compound (S)-3-(1-Aminoethyl)-8-chloro-2-cyclopropylisoquinolin-1(2H)-one (1.012 g, 3.852 mmol),6-chloro-5-iodopyrimidine-4-amine (1.04 g, 4.07 mmol)And triethylamine (993 mg, 7.606 mmol) in n-BuOH (10 mL)The mixture was heated to 125 C and stirring was continued for 48 hours.Then cool to room temperature,Concentrated under reduced pressure,The residue obtained was subjected to silica gel column chromatography (DCM/MeOH (v/v) = 100/1)The crude product obtained was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/2)The title compound was obtained as a pale yellow solid (430 mg. 23.1%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; Wu Weibin; (84 pag.)CN105130966; (2019); B;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 108381-23-3, Ethyl 2-chloro-4,6-dimethylpyrimidine-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, Safety of Ethyl 2-chloro-4,6-dimethylpyrimidine-5-carboxylate, blongs to pyrimidines compound. Safety of Ethyl 2-chloro-4,6-dimethylpyrimidine-5-carboxylate

General procedure: To a solution of appropriate 10 (0.5 g, 2.56 mmol) in dry CH3CN (30 ml), dry K2CO3 (1.06 g, 7.69 mmol) and propargyl alcohol (0.2 ml, 3.84 mmol) were added in that sequence and reaction mixture was refluxed overnight. After completion of reaction (TLC), CH3CN was removed under vacuum. Water was then added to the residue and the product extracted with DCM (2 x 20 ml). Solvent was removed to obtain crude 11, which was purified by column chromatography over silica 60-120 using 20:80 (ethyl acetate/hexane) as eluent to isolate analytically pure 11a-f.

The synthetic route of 108381-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chopra, Rakesh; De Kock, Carmen; Smith, Peter; Chibale, Kelly; Singh, Kamaljit; European Journal of Medicinal Chemistry; vol. 100; 1; (2015); p. 1 – 9;,
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Pyrimidine – Wikipedia

Reference of 4983-28-2, 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.4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, molecular weight is 130.53, as common compound, the synthetic route is as follows.

A solution of 2-chloropyrimidin-5-ol (70% purity, 7.5g, 40mmol) in DMF (15mL, 190mmol), under argon, was cooled to 0C. Cesium Carbonate (14. Og, 43mmol) was added, portionwise, and the mixture was stirred for 5min at 0C then lOmin at r.t.. The mixture was cooled back back down to 0C and benzyl bromide (5.1mL, 43mmol) was added, portionwise. The reaction was stirred at 0C for 15min, then allowed to warm to r.t. and stirred for a further 90min. The solvent was removed in vacuo and the residue partitoned between EtOAc and water. The organic phase was separated, washed with water:brine(l : 1), dried (MgS04), and the solvent removed in vacuo. Trituration from a combination of Et20 and IH, and further trituration of the motherliquer after concentration in vacuo, afforded the title compound in two crops: RT = 3.54 min; m/z (ES ) = 221.0 [M+ H]+.

Statistics shows that 4983-28-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-hydroxypyrimidine.

Reference:
Patent; PROSIDION LIMITED; BARBA, Oscar; BELL, James, Charles; DUPREE, Tom, Banksia; FRY, Peter, Timothy; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; GATTRELL, William; JEEVARATNAM, Revathy, Perpetua; KEILY, John; KRULLE, Thomas, Martin; MCDONALD, Russell, Walker; MORGAN, Trevor; RASAMISON, Chrystelle, Marie; SCHOFIELD, Karen, Lesley; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2011/147951; (2011); A1;,
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Synthetic Route of 4595-60-2, 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 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 2-(6-Bromopyridin-2-yl)pyrimidine Under argon, 54.5 ml (137.1 mmol) of a 2.5 molar solution of N-BuLi in 70 ml of THF were diluted with 70 ml of THF. At <-70 C., 32.5 g (137.1 mmol) of 2,6-dibromopyridine dissolved in 150 ml of THF were added dropwise. The mixture was stirred for 15 min and, still at <-70 C., 19.2 ml (107 mmol) of a 5.6-molar solution of zinc chloride in diethyl ether were then added. The mixture was allowed to thaw, a solution of 17.4 g (109 mmol) of bromopyrimidine in 50 ml of THF and a suspension of 3.9 g (3.4 mmol) of tetrakis(triphenylphosphine)palladium in 50 ml of THF were added. The mixture was boiled at reflux for 4 h and, after cooling, Na EDTA in water and dilute aqueous sodium hydroxide solution to pH=10 were added. The mixture was filtered off with suction to remove undissolved material, the aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried with MgSO4 and concentrated by evaporation. The residue was recrystallized from 60 ml of benzotrifluoride which involved brief heating to boiling point with activated carbon and hot filtration. Yield: 14.82 g (52% of theory), logP (HCOOH) 1.3 1H-NMR (CD3CN): 7.4 (t, 1H), 7.65 (d, 1H), 7.8 (dd, 1H), 8.4 (d, 1H), 8.9 (m, 2H) According to the analysis of related databases, 4595-60-2, the application of this compound in the production field has become more and more popular. Reference:
Patent; Bayer CropScience AG; US2011/212949; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia