Pyrimidines

Electric Literature of 153286-94-3, 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.153286-94-3, name is 5-Ethynylpyrimidine, molecular formula is C6H4N2, molecular weight is 104.1094, as common compound, the synthetic route is as follows.

General procedure: To a stirring solution of 3 (1 eq.) in MeOH (5 vol) was added alkyne(1 eq.) followed by 100 mM aq. CuSO4 (5 mol %) and 100 mM aq. sodium ascorbate (10 mol %). The reaction was diluted with DCM (10 mL). The tan ppt was then collected by filtration. The organic layer filtrate was evaporated to give a crude crystalline solid. The ppt and crystals were combined and purified by MPLC over C18 silica gel (Grace Reveleris X2, A: H2O + 0.1% TFA, B: ACN + 0.1% TFA, 5-30% B). Theeluent was removed by lyophilisation to give a colourless powder (86 mg, 56%). LCMS:Rt = 1.99 min, 99 A% 254 nm, [M + H]+ = 300.8. 1HNMR (600 MHz, DMSO-d6) delta 9.19 (s, 2H), 9.18 (s,1H), 8.70 (s, 1H), 8.07 (s, 1H), 4.94 (dd, J= 6.5, 4.7 Hz, 2H), 4.79 (dd, J =6.5, 4.8 Hz, 2H), 2.00 (s, 3H). 13C NMR (150 MHz, DMSO-d6) delta 157.7, 153.3, 151.3, 140.8, 138.4, 133.3, 124.7, 123.7, 49.1,45.9, 13.0. HRMS calcd for C12H12N8NaO2 [M + Na]+, 323.0975; found, 323.0966.

Statistics shows that 153286-94-3 is playing an increasingly important role. we look forward to future research findings about 5-Ethynylpyrimidine.

Reference:
Article; Jarrad, Angie M.; Karoli, Tomislav; Debnath, Anjan; Tay, Chin Yen; Huang, Johnny X.; Kaeslin, Geraldine; Elliott, Alysha G.; Miyamoto, Yukiko; Ramu, Soumya; Kavanagh, Angela M.; Zuegg, Johannes; Eckmann, Lars; Blaskovich, Mark A.T.; Cooper, Matthew A.; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 96 – 102;,
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Pyrimidine – Wikipedia

Electric Literature of 89793-12-4, 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 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of ethyl 2-(1-(3-fluorophenyl)cyclohexylamino)pyrimidine-5-carboxylate To a solution of 1-(3-fluorophenyl)cyclohexanamine hydrochloride (2.29 g 10 mmol) in Dioxane (50 ml) was added ethyl 2-chloropyrimidine-5-carboxylate (1.87 g, 1.0 eq) and DIPEA (2.58 g, 2.0 eq). The mixture was heated overnight at 110-120° C. The resulting mixture was directly purified on silica gel column to afford the coupled product as white solid (1.37 g, 40percent)

According to the analysis of related databases, 89793-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; Anderson, Kenneth C.; Hideshima, Teru; US2015/105358; (2015); A1;,
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Application of 444731-75-3, Adding some certain compound to certain chemical reactions, such as: 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine,molecular formula is C14H14ClN5, 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 444731-75-3.

In the reaction flask, N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine29 g and 27 g of potassium carbonate and 19 g of 3-sulfonate amine 4-methyl-aniline were added to 300 mL of ethanol.The reaction was stirred at room temperature for 1.5 h under nitrogen.Then slowly add concentrated hydrochloric acid solution (100mL), after the addition is completed, slowly stir to warm up to reflux state, HPLC monitoringThe residual amount of N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-carbazole-6-amine in the reaction system is less than 1%, and is cooled to about 0 C, and the temperature is kept stirring. 30min,A large amount of solid precipitated under stirring, and the reaction solution was quickly filtered.The filter cake was washed several times with cold ethanol 10 mL.The filter cake was dried to give 36.7 g of pazopanic hydrochloride.

According to the analysis of related databases, 444731-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jinan Ai Si Pharmaceutical Technology Co., Ltd.; Peng Lizeng; Mao Longfei; Liu Xiaofei; Yao Xiaojun; Liu Huanxiang; Bai Qifeng; Liang Lixian; (17 pag.)CN110028495; (2019); A;,
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Pyrimidine – Wikipedia

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 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H5ClN4

The preparation method of the compound e33 comprises the following steps: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol of hydrazine to 10 mL of microwave reaction In the tube,Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e33.The compound e33 is a white solid with a yield of 44%.

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
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Synthetic Route of 63200-54-4, 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. 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, 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.

Preparation method reference Example 1, wherein,Cyclopropylamine is replaced with cyclobutylamine,The reaction temperature is increased from 30 C to reflux. Got a white solid. Yield: 80%. 2,4-Dichloro-5H-pyrrolo [3,2-d] pyrimidine (600 mg, 3.19 mmol) was placed in a round bottom flask,Tetrahydrofuran THF (20 mL) was added to dissolve, and cyclopropylamine (218 mg, 3.83 mmol) and N-diisopropylethylamine DIEA (823 mg, 6.38 mmol)30 C reaction 24h. Treatment: The reaction mixture was removed under reduced pressure,The residue was subjected to column chromatography (petroleum ether: ethyl acetate = 2: 1) to give a white solid. Yield: 63%.

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 63200-54-4, 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Zhengzhou University The First Affiliated Hospital; Kan Quancheng; Tian Xin; Zhang Xiaojian; Cheng Weiyan; Du Yue; Yang Zhiheng; Yuan Yongliang; (12 pag.)CN107312006; (2017); A;,
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Pyrimidine – Wikipedia

Electric Literature of 696-07-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 696-07-1 as follows.

5-Iodouracil (0.10 g, 0.42 mmol) was suspended in dry MeCN (2.1 mL) and N,O-bis(trimethylsilyl)acetamide (0.25 mL, 1.05 mmol) was added under nitrogen atmosphere. When the reaction mixture turned clear, bromodiphenyl methane (0.15 g, 0.63 mmol) and a catalytic amount of I2 were added and the reaction mixture was heated at 84 C. for 4 hrs. After cooling to room temperature, the mixture was concentrated under reduced pressure, diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc (3*15 mL), the combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 60:40) to afford the title compound (0.15 g, 87%) as white solid. 1H NMR (400 MHz, CDCl3): delta 7.02 (s, 1H), 7.14-7.18 (m, 4H), 7.38-7.45 (m, 6H), 7.46 (s, 1H), 8.58 (s, 1H). MS (ESI) in/Z: 405 [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,696-07-1, its application will become more common.

Reference:
Patent; Piomelli, Daniele; Realini, Natalia; Mor, Marco; Pagliuca, Chiara; Pizzirani, Daniela; Scarpelli, Rita; Bandiera, Tiziano; US2015/111892; (2015); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22276-95-5, 5-Bromo-4-chloro-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, Product Details of 22276-95-5, blongs to pyrimidines compound. Product Details of 22276-95-5

General procedure: N,O-Bis(trimethylsilyl)acetamide (488.2 mg, 586.8 muL, 2.40 mmol) was added to a suspension of 7-bromo-6-chloro-7-deazapurine (464.9 mg, 2.00 mmol) in 20 mL dry acetonitrile. Afterwards, the solution was stirred for 15 min at room temperature in an argon atmosphere,followed by the addition of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-Dribofuranose(1.21 g, 2.40 mmol) and trimethylsilyl trifluoromethanesulfonate(533.4 mg, 434.4 muL, 2.40 mmol). The reaction mixture was heated for 2 h at 80 C under argon with vigorous stirring. After glycosylation, the solution was left to cool down and diluted with 400 mL ethyl acetate. The organic phase was sequentially washed twice with a saturated sodium hydrogen carbonate solution and brine. Subsequently, the organic layer was dried with magnesium sulfate and the solvent was removed under vacuum, to afford the crude nucleoside. Purification by column chromatography on silica gel with hexane/ethylacetate (2:1) as eluent yielded the product as colorless solid (864.0 mg,1.28 mmol, 64%). 1H NMR (300 MHz, DMSO-d6) delta 8.62 (1H, s), 8.32(1H, s), 8.00-7.84 (6H, m), 7.69-7.61 (3H, m), 7.54-7.40 (6H, m), 6.73(1H, d, J=5.0 Hz), 6.32-6.28 (1H, m), 6.16-6.11 (1H, m), 4.90-4.85(1H, m), 4.84-4.65 (2H, m); 13C NMR (75 MHz, DMSO-d6) delta 165.4,164.7, 164.5, 151.4, 151.0, 150.3, 134.0, 133.9, 133.6, 129.4, 129.4,129.3, 129.2, 129.2, 128.8, 128.6, 128.2, 114.9, 88.1, 86.6, 79.3, 73.5,70.6, 63.4; HRMS (ESI): m/z calcd for C32H24BrClN3O7 [M+H]+676.0481, found 676.0489.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Lelle, Marco; Otte, Maik; Thon, Susanne; Bertinetti, Daniela; Herberg, Friedrich W.; Benndorf, Klaus; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1704 – 1713;,
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Pyrimidine – Wikipedia

Electric Literature of 5751-20-2, 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. 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, 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.

Example 11 Synthetic route

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 5751-20-2, 2-(Methylthio)pyrimidin-4(3H)-one.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2011/133444; (2011); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 31519-62-7, 2-Pyrimidinecarboxylic acid, 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, 31519-62-7, blongs to pyrimidines compound. COA of Formula: C5H4N2O2

A flask was charged with pyrimidine-2-carboxylic acid (63.2 mg, 0.509 mmol, 1.00 equiv), DCM (5 mL), and thionyl chloride (121 mg, 1.02 mmol, 2.00 equiv). The resulting solution was stirred for 1 h at 40 C. The resulting mixture was concentrated under reduced pressure to provide 72.0 mg (99% yield) of pyrimidine-2-carbonyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31519-62-7, its application will become more common.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
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Pyrimidine – Wikipedia

Application of 5305-59-9, Adding some certain compound to certain chemical reactions, such as: 5305-59-9, name is 6-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 5305-59-9.

General procedure: 2-Amino-4-chloropyrimidine (55) (13.0g, 100mmol) was added to a 57wt.% aqueous solution of hydriodic acid (115ml, 1.00mol) at 0C and the mixture was stirred at room temperature for 3h. The mixture was cooled to 0C and the resulting precipitate was removed by filtration and taken up in cold 5N aqueous Na2CO3 (200ml). The mixture was extracted with EtOAc (3×500ml) and the combined organic layers were concentrated under reduced pressure to deliver 2-amino-4-iodopyrimidine (21.1g, 95.0mmol, 95% yield) as a white solid.

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
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Pyrimidine – Wikipedia