Pyrimidines

Application of 24415-66-5 , The common heterocyclic compound, 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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.

The preparation method of the compound e22 comprises the steps of: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol.1-benzyl-5-methoxy-1H-indole was added to a 10 mL microwave reaction 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 e22.The compound e22 is a yellow solid with a yield of 89%.

The synthetic route of 24415-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
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Application of 1004-39-3, 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.1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, molecular weight is 142.18, as common compound, the synthetic route is as follows.

3.79 g (10 mmol) of pleuromutilin were added to a 250 mL flask.2.1 g (11 mmol) of p-toluenesulfonyl chloride was added to 60 mL of dichloromethane, and the temperature was raised to 45C.A 2.5 ml NaOH solution having a concentration of 0.01 mol/ml was slowly added dropwise with stirring, and a large amount of white substance was generated after the reaction for 40 minutes.At room temperature, 1.44 g of 4,6-diamino-2-mercaptopyrimidine and 20 mL of methanol were added and the reaction was stirred at room temperature for 36 h.After the reaction, the solvent was evaporated under reduced pressure. The crude product was extracted with 30 mL of ethyl acetate and 10 mL of solvent.Take three times, combine the organic phase,30 mL of a saturated NaHCO 3 solution was added and the mixture was filtered to obtain the compound of Formula I (4.77 g, yield 95%).

The chemical industry reduces the impact on the environment during synthesis 1004-39-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Lanzhou Husbandry And Veterinary Drugs Institute; Shang Ruofeng; Yi Yunpeng; Liu Yu; Ai Xin; Yang Zhen; Liang Jianping; (13 pag.)CN105622524; (2018); B;,
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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 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H4Cl2N2

tert-Butyl (3R.4S 4-r(6-chloro i–5-methylpyrimidin-4-yl)oxyl-3- fluoropiperidine-1 -carboxylate (racemic)To a solution of ie -butyl-(3,4-cis)-3-fluoro-4-hydroxy-piperidine-1 -carboxylate(racemic) (Preparation 1 ) (1.0 g, 4.6 mmol) and 4,6-dichloro-5-methylpyrimidine (818 mg, 5.02 mmol) in anhydrous tetrahydrofuran (23 mL) was added sodium hydride (201 mg, 5.02 mmol, 60% dispersion in mineral oil) in two portions at 0 degrees Celsius. After 18 hours, the reaction mixture was quenched with saturatedaqueous ammonium chloride and diluted with water. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a pale yellow oil (1.56 g, 99%). 1 H NMR (400 MHz, deuterochloroform) delta 1 .46 (s, 9 H), 1.84 – 1 .91 (m, 1 H), 2.04 – 2.17 (m, 1 H), 2.24 (s, 3 H), 3.09 – 3.22 (m, 1 H), 3.29 – 3.43 (m, 1 H), 3.78 – 4.01 (m, 1 H), 4.09 – 4.20 (m, 1 H), 4.74 – 4.93 (m, 1 H), 5.31 – 5.43 (m, 1 H), 8.36 (s, 1 H). LCMS: (ES+): 346.4 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 4316-97-6.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton; WO2011/61679; (2011); 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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5ClN2O2

A microwave reaction vessel was charged with 3-(methoxy-phenyl)-propylamine (1.44g,8.7mmol), 2-chloro-pyrimidine-5-carboxylic acid methyl ester (Maybridge, lg, 5.8mmol), potassium acetate (1.62g, 16.5mmol) and methanol (10ml). The mixture was heated to 150C for lh in a microwave oven, then cooled to rt and quenched with cold water (4ml). The precipitate was collected by filtration and washed with water and cold methanol to afford the desired product (1.73g, 99% yield).

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, 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GILLESPIE, Paul; MICHOUD, Christophe; RUPERT, Kenneth Carey; THAKKAR, Kshitij Chhabilbhai; YI, Lin; WO2012/123467; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13036-57-2, 2-Chloro-4-methylpyrimidine, 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, 13036-57-2, blongs to pyrimidines compound. Computed Properties of C5H5ClN2

Example 11, Step E[00133] A solution of compound 11f (68 mg, 0.2 mmol), 2-chloro-4-methylpyrimidine (31 mg, 0.24 mmol), Pd2(dba)3 (22.85 mg, 0.025 mmol), Xant-phos (28.9 mg, 0.05 mmol) and Cs2C03 (98 mg, 0.3 mmol) in dioxane (3 mL) was heated to reflux for 4 hrs under N2. After cooling to r.t., the mixture was diluted with H20 (10 mL) and extracted with EtOAc (10 mL*2), the combined organic layers were dried over Na2S04, concentrated in vacuo and purified by preparative TLC (EtOAc: PE = 2:1 ) to give product 11g (52.4 mg, 62%).[00134] This compound was characterized by mass spectroscopy (MS) in accordance with the procedures described herein. Mass spectroscopy indicated MS (ESI): m/z 431 (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,13036-57-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2240-25-7, 4-Amino-5-bromopyrimidin-2(1H)-one, 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-Amino-5-bromopyrimidin-2(1H)-one, blongs to pyrimidines compound. Safety of 4-Amino-5-bromopyrimidin-2(1H)-one

EXAMPLE 694-amino-5-(2-(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methylthio)ethylamino)pyrimidin-2(1H)-one 40A solid mixture of 34 (100 mg, 0.306 mmol) and 5-bromocytosine (58 mg, 0.305 mmol) was heated at 150¡ã C. for 4 hours. After the reaction had cooled to room temperature, the product was purified by preparative HPLC to give the title compound 40 as the formate salt in 8.4percent yield (11 mg). 1H NMR (DMSO-d6/D2O) delta (ppm): 8.31 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 6.62 (s, 1H), 5.85 (d, 1H, J=5.6 Hz), 4.70 (dd, 1H, J=5.2, 5.6 Hz), 4.13 (m, 1H), 4.00 (m, 1H), 2.90 (m, 4H), 2.65 (m, 2H). MS calc 435.46; found 436 (MH)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2240-25-7, 4-Amino-5-bromopyrimidin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; METHYLGENE INC.; US2008/132525; (2008); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 89793-12-4 ,Some common heterocyclic compound, 89793-12-4, molecular formula is C7H7ClN2O2, 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.

To a solution of compound 5 (9.6 g, 26 mmol), 2-Cl-pyrimidine (4.9 g, 26 mmol) in 150 ml 1 ,4-Dioxane was added DIPEA (7.7 g, 60 mmol). The mixture was stirred at 110¡ã C. overnight. ECMS was used to monitor the reaction to completion. Water (50 ml) was added and the mixture was extracted with EtOAc. The combined organic extracts were washed and dried. The target compound 6 (11 g, 90percent) was purified by flash chromatography with PE/EA from 30:1 to2:1.

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. 89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Jones, Simon Stewart; Yang, Min; Tamang, David Lee; US2015/105384; (2015); A1;,
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Synthetic Route of 22536-61-4, 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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.

0.40 g of 2-chloro-5-methylpyrimidine was dissolved in 15 ml of carbontetrachloride and then added with 0.83 g of N-bromosuccinimide and 0.05 g of azobisisobutyronitrile, followed by heating under reflux for 8 hours. The reaction mixture was cooled down to room temperature and then filtrated, followed by the filtrate being concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.27 g of 5-bromomethyl-2-chloropyrimidine represented by above formula.1H-NMR (CDCl3, TMS) , delta (ppm) : 4.43 (2H, s), 8.67 (2H, s)

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1555259; (2005); A1;,
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Pyrimidine – Wikipedia

Application of 137234-74-3, 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. 137234-74-3, name is 4-Chloro-6-ethyl-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

PREPARATION EXAMPLE 19: Preparation of 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine A solution of 5 g of 6-chloro-4-ethyl-5-fluoropyrimidine, 6.65 g of NBS, and 0.51 g of AIBN in 50 ml of methylene chloride was stirred for 12 hrs under reflux. The reaction was cooled to room temperature and added with 30 ml of pure water. The organic layer was obtained, and the aqueous fraction was extracted with 30 ml of methylene chloride. The organic layers thus obtained were pooled and washed with 30 ml of 10 % sodium metabisulfite, and then with pure water. After dehydration with a desiccant, the obtained product was concentrated under reduced pressure to afford 6.95 g of the title compound (Yield: 95.1%). 1H NMR (CDCl3) delta 8.80(s, 1H), 5.35(q, 1H), 2.08(d, 3H) ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137234-74-3, its application will become more common.

Reference:
Patent; Boryung Pharmaceutical Co., Ltd.; KIM, Ji Han; KIM, Je Hak; LEE, Joon Kwang; JUNG, Hahn-Sun; HAN, Nam Seok; PARK, Yong; KANG, Seung-Hoon; JEONG, Hee Jin; LEE, Kyung-Tae; CHOI, Hye Eun; CHI, Yong Ha; LEE, Joo Han; PAIK, Soo Heui; EP2754655; (2014); A2;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4433-40-3, name is 5-(Hydroxymethyl)pyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. Quality Control of 5-(Hydroxymethyl)pyrimidine-2,4(1H,3H)-dione

To a suspension of 5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (35.0 g, 246.3 mmol) in toluene (100 mL) was added POCl3 (105 mL, 1147 mmol) followed by slow addition of DIPEA (120 mL, 689 mmol), the mixture was tirred at 110-120 oC for 8 h. Then the reaction mixture was poured to a mixture of water (100 mL) and ethyl acetate (200 mL), extracted with ethyl acetate (1 L ¡Á 2), washed with brine (200 mL ¡Á 3), died with Na2SO4. Purified by silica gel (DCM) to give 2,4-dichloro-5- (chloromethyl)pyrimidine as light yellow solid (22 g), yield 46percent. LC/MS (ESI) m/z = 197 (M + H) +.

The synthetic route of 4433-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; GRAY, Nathanael, S.; LIANG, Yanke; CHOI, Hwan, Geun; SUNDBERG, Thomas; SHAMJI, Alykhan; XAVIER, Ramnik; FISHER, David E.; (251 pag.)WO2018/9544; (2018); A1;,
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