Month: February 2021

Synthetic Route of 51940-64-8, Adding some certain compound to certain chemical reactions, such as: 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate,molecular formula is C7H6Cl2N2O2, 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 51940-64-8.

General method for synthesis of 2-amino-4-chloropyrimidine-5-carboxylate: To a stirred solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (1.6 g, 7.24 mmol) in 1,4- dioxane (15 mL) at 0-5 C under argon, ammonium hydroxide (28-30%, 2.56 mL, 21.72 mmol) is added slowly and the resulting mixture is stirred from 0 C to RT for 2 h. The reaction is complete based on TLC (30% EA/Hex, Rf = 0.3 for ethyl 2-amino-4-chloropyrimidine-5-carboxylate (Hinge-1); Rf = 0.5 for ethyl 4-amino-2-chloropyrimidine- 5-carboxylate) and LC-MS analysis. The mixture is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2S04 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is loaded to the top of silica gel packed in a glass column and eluted with 0-100% ethyl acetate/hexanes to afford ethyl 2-amino-4-chloropyrimidine-5-carboxylate (Hinge-1).[00669] The other regio isomer, ethyl 4-amino-2-chloropyrimidine-5-carboxylate, is also isolated.

According to the analysis of related databases, 51940-64-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); 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.1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.COA of Formula: C5H4Cl2N2

Example 7; Preparation of 7-(4-chlorophenyl)-5-methyl-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one; A. Preparation of 4-chloro-6-hydrazinyl-2-methylpyrimidine; To a stirred solution of 4,6-dichloro-2-methylpyrimidine (1.63 g, 10.0 mmol) in THF (25 mL) at room temperature under argon was added H2NNH2 (0.64 g, 20.0 mmol). The reaction mixture was stirred at room temperature under argon overnight. Analysis by HPLC/MS indicated that the reaction was complete. The solvent was evaporated, and the residue was coevaporated with toluene (2¡Á5 mL) then THF (5 mL), and then dried under vacuum. The crude title compound was used directly in the next step. HPLC/MS: retention time=0.77 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, 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, Formula: C4HCl2FN2, blongs to pyrimidines compound. Formula: C4HCl2FN2

A solution of 3-nitroaniline and 2,4-dichloro-5-fluoro-pyrimidine in MeOH was stirred for 2 hours at 70 C. The mixture was diluted with water and the resulting precipitate was filtered to give 2-chloro-N4-(3-nitrophenyl)-5-fluoro-2,4-pyrimidineamine as a pale brown solid. 1H NMR (DMSO): delta 10.34 (s, 1H), 8.73 (d, 1H, J=2.4 Hz), 7.66-8.29 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 55583-59-0, 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. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (358 mg, 2.00 mmol), 5′-m-terphenylboronic acid (1.22 g, 4.45 mmol), sodium carbonate (1.06 g) Add ethanol (5 mL) and distilled water (5 mL) to a solution of 10.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL) at After stirring for 20 hours under heating and reflux conditions under an argon atmosphere, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (10 mL). Thereafter, the whole organic layer is combined, saturated aqueous sodium chloride solution (10 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration and the filtrate after filtration is concentrated under reduced pressure The The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Di ([1,1 ‘: 3′, 1′-terphenyl] -5’-yl) pyrimidine-2,5-diamine(1.01 g, 90% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6693-08-9, Adding some certain compound to certain chemical reactions, such as: 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine,molecular formula is C4Cl3FN2, 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 6693-08-9.

The thiophene (300 mg, 3.57 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL).After cooling to -15 C, n-butyllithium (1.4 mL, 3.57 mmol, 2.5 mol/L) was added.Stir at this temperature for 1 hour, then add ZnCl2-TMEDA (300 mg,1.18 mmol), stirring at room temperature for 1 hour, then adding palladium dichloride (65 mg, 0.36 mmol),Triphenylphosphine (188 mg, 0.71 mmol)And 5-fluoro-2,4,6-trichloropyrimidine (790 mg, 3.92 mmol),The resulting mixture was heated to 55 C under nitrogen to stir the reaction overnight.Water (50 mL) was added to the reaction mixture, and the mixture was evaporated.The combined organic phases were washed with brine (50 mL).Dry over anhydrous sodium sulfate, filter and concentrate under reduced pressure.The residue obtained is purified by silica gel column chromatography (pure petroleum ether).The title compound was obtained as a white solid(366 mg, 41%).

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. 6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 944129-00-4, Adding some certain compound to certain chemical reactions, such as: 944129-00-4, name is Methyl 6-amino-2-chloropyrimidine-4-carboxylate,molecular formula is C6H6ClN3O2, 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 944129-00-4.

6-Amino-2-chloropyrimidine-4-carboxylic acid methyl ester (2.25 g, 12 mmol, 4-chloro-2-fluoro-3-methoxyphenylboronic acid (3.27 g, 16 mmol), and bis(triphenylphosphine)palladium(II) dichloride (842 mg, 1.2 mmol) were combined in 12 mL of 1,2-dimethoxyethane and 12 mL of water. The reaction mixture was heated at 80 C. for 2 h and the cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried, and concentrated under vacuum. The product was purified by flash chromatography on silica gel to yield the title compound (2.0 g, 53.5% yield): mp 188-190 C.: 1H NMR (CDCl3) delta 7.66 (dd, 1H), 7.22 (dd, 1H), 7.14 (s, 1H), 5.25 (br s, 2H), 4.0 (s, 3H), 3.99 (s, 3H).

According to the analysis of related databases, 944129-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; US2009/88322; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

Preparation 109; 4-Chloro-5-iodo-7H-pyrrolo|”2.3-Patent; ELI LILLY AND COMPANY; WO2008/140947; (2008); 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. 23945-44-0, name is 2,4-Dihydroxypyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 23945-44-0

The starting material Compound G was introduced in the reactor with POC13 and about 3 equivalents of PC15. In this case POC13 acted as solvent due to the very low solubility of Compound G in many organic solvents. The reaction temperature was increased from 80 C to 105 C in 3 hrs and then left at 105 C for additional 1-2 hrs. When the reaction completed, POC13 was distilled. Toluene was added to the residue and distilled in order to reduce the amount of POC13. Crude Compound F-i was distilled at around 7-8 mbar, with ajacketed temperature of about 130-13 5 C. Average yield 72% and average purity 94.9 % by GC-FID.

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, 23945-44-0, 2,4-Dihydroxypyrimidine-5-carboxylic acid.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; SRAN, Arvinder; CHEN, Ying; POGGIALI, Daniele; FUMAGALLI, Tiziano; (52 pag.)WO2019/213545; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1074-41-5 ,Some common heterocyclic compound, 1074-41-5, molecular formula is C5H7N3OS, 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: A mixture of 6-amino-2-(alkylthio)pyrimidin-4(3H)-one 5 (1 mmol),1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 6 (1 mmol),arylaldehyde (1 mmol) and [gamma-Fe2O3HAp-SO3H] (0.05 g) in EtOH (10 mL) was heated under reflux. The progress of the reaction was monitored by TLC (EtOAc/petroleum: 2/1). After completion ofthe reaction, the catalyst was separated from the reaction mixture by external magnet and reused in the next run. The reaction mixture was cooled, and the solid obtained was recrystallised from EtOH/H2O to give the desired pure product.

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. 1074-41-5, 6-Amino-2-(methylthio)pyrimidin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mamaghani, Manouchehr; Taati, Zahra; Rasoulian, Mona; Yousefizad, Javad; Toraji, Nooshin; Mohsenimehr, Mona; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 40; 1; (2016); p. 29 – 34;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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. Quality Control of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (0.2 g, 1.29 mmol) in anh THF (10 mL), 2-(piperidin-1-yl)ethanol (0.258 mL, 1.94 mmol) and triphenylphosphine (0.51 g ,1.94 mmol) were sequentially added. The reaction mixture was cooled to 0 C and diisopropylazodicarboxylate (0.38 mL ,1.94mmol) was added dropwise. The mixture was stirred for 30 min. at 0 C and kept overnight at 4 C. The solvent was removed at reduced pressure and the residue was dissolved in DCM and washed with diluted HCl 1N. The aqueous phase was separated, basified and extracted with DCM. The organic phase was separated, dried and the solvent was removed under reduced pressure to give a residue that was purified by flash chromatography eluting with (EtOAc/Petroleum ether, 8:2) to yield 4-chloro-1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidine (146 mg, 55 mmol, 42 %) as an oil that solidifies “on standing”.

With the rapid development of chemical substances, we look forward to future research findings about 5399-92-8.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; Diaz-Fernandez, Jose-Luis; Almansa, Carme; Corbera Arjona, Jordi; EP2733143; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia