Pyrimidines

Electric Literature of 53554-29-3, 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. 53554-29-3, name is Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

A mixture of 4-hydroxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (50 g, 0.234 mmol), POC13 (110 mL, 1.17 mmol) and diethylamide (70 mL, 0.28 mmol) was refluxed for 5h. The solvent was removed under vacuum and the residue was dissolved in ice H2O and cautiously neutralized with aqueous NaHCO3. After extraction with EtOAc (3×400 mL), the organic extracts were combined, dried and concentrated to give 4-chloro-2- (methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester as a yellow solid (42 g, 77% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53554-29-3, Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3934-20-1, 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. 3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

To a solution of ethyl 3-methyl-iH-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N- dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature. The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (x2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 2 as a white solid (5.47 g, 42 %); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCls) delta 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, / = 5.4 Hz), 7.87 (1H, d, / = 5.4 Hz), 2.59 (s, 3H).

According to the analysis of related databases, 3934-20-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENOSCO; OSCOTEC, INC.; CHOI, Jang-Sik; HWANG, Hae-Jun; LEE, Eunho; LEE, Jaekyoo; SONG, Ho-Juhn; KIM, Se Won; KIM, Jung-Ho; KOH, Jong, Sung; CHANG, Sunhwa; LEE, Tae-im; CHOI, Yung-geun; HAN, Ik-hwan; LEE, Jaesang; WO2013/109882; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13036-57-2 ,Some common heterocyclic compound, 13036-57-2, molecular formula is C5H5ClN2, 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 containing 37 g (188 mmol) of methyl 3,5-bis(methyloxy)benzoate and 300 mL of THF at 00C was added 395 mL (395 mmol) of a 1.0 M solution of LHMDS in THF. To this mixture, a solution containing 29 g (226 mmol) of 2-chloro-4- methylpyrimidine and 100 mL was added dropwise over about 30 min. The reaction mixture was allowed to stir for an additional 30 min and quenched by the addition of 100 mL of MeOH. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc and water. The combined organic layers were dried over MgSO4 and filtered, washing the filter cake with copious amounts of EtOAc and DCM to dissolve precipitated product. The solvents were removed under reduced pressure and the resulting orange solid was triturated from EtOAc to give 46.5 g (85%) of 1-[3,5-bis(methyloxy)phenyl]-2-(2-chloro-4-pyrimidinyl)ethanone as a light tan solid, which exists as a mixture of ketone and enol tautomers: MS (ESI): 293.29 (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; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 32980-71-5, 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.32980-71-5, name is Perchloropyrimido[5,4-d]pyrimidine, molecular formula is C6Cl4N4, molecular weight is 269.9, as common compound, the synthetic route is as follows.

the entire chlorine pyrimido [5, 4 – d] pyrimidine (13.1 g, 48.9 mmol), piperidine, CuI (0.28 g, 1.5 mmol), Cs2 CO3 (16.0 g, 48.9 mmol) is put into the 250 in two mouth flask, add 100 ml nitrobenzene as the reaction solvent, under the protection of nitrogen, 180 C lower reaction 16 h, oil pump by reducing pressure after the reaction of the nitrobenzene solvent, PE_DCM=6:1 to column chromatography, obtaining the solid 17.0 g, yield of 95.0%, the selectivity 99%

Statistics shows that 32980-71-5 is playing an increasingly important role. we look forward to future research findings about Perchloropyrimido[5,4-d]pyrimidine.

Reference:
Patent; Dalian Wanfu Pharmaceutical Co., Ltd.; Sun Qingfa; (9 pag.)CN106946887; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 51-20-7, 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 51-20-7, name is 5-Bromouracil. This compound has unique chemical properties. The synthetic route is as follows.

5-bromouracil (6.0 g, 31.4 mmol) was mixed with PCl5 (16.4 g, 87.9 mmol) in a reaction flask.Add 1,1,2-trichloroethane (50 mL),The reaction mixture was heated to reflux.During the reaction, the mixture changed from a suspended state to a pale yellow clear solution.At this point TLC showed that the starting material was completely reacted.Drop to room temperature.Slowly pour the reaction mixture into stirred ice water.Stir for 1h,Add DCM (3 x 50 mL) for extraction.The organic layer was dried over anhydrous MgSO4.Evaporate the solvent,A pale yellow transparent liquid was obtained.Further purified on a silica gel column.Obtaining a colorless transparent liquid,That is, Compound 2 (yield 99.5%, purity 97%).

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 51-20-7, 5-Bromouracil.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Ma Qingtong; Shan Xiaoyan; Chen Xudong; Chen Yu; (9 pag.)CN108117523; (2018); A;,
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. 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. Computed Properties of C6H3Cl2N3

2,4-Dichloro-5H-pyrrolo [3,2-d] pyrimidine(600 mg, 3.19 mmol) was placed in a round bottom flask,N, N-dimethylformamide DMF (5 mL) was added to dissolve it,Methyl iodide (544 mg, 3.83 mmol) and cesium carbonate (520 mg, 1.60 mmol) were added successively and the reaction was stirred at room temperature for 24 h.Treatment: The reaction solution was added to water and extracted with ethyl acetate,The organic phase was collected, dried over anhydrous sodium sulphate, filtered off with suction and concentrated. A yellow solid. Yield: 91%.

With the rapid development of chemical substances, we look forward to future research findings about 63200-54-4.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 35265-83-9, 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 35265-83-9 as follows.

Reference Example 31 4-Butylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine In DMF was dissolved 700 mg (3.2 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine, and then an aqueous solution of 548 mg (7.5 mmol) of butylamine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction mixture was stirred at 0C. for one hour and then allowed to resume room temperature, followed by stirring for one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml*3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane={fraction (1/10)}) to give 698 mg (yield: 85.4%) of the title compound. NMR (delta, CDCl3): 0.98 (3H, t, J=7.3 Hz), 1.41-1.50 (2H, m), 1.64-1.72 (2H, m), 2.42 (3H, s), 3.64-3.69 (2H, m), 4.99 (1H, br), 7.35 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35265-83-9, its application will become more common.

Reference:
Patent; NAKASHIMA, YOSHIHARU; FUJITA, TAKASHI; HIZUKA, MICHIYO; IKAWA, HIROSHI; HIRUMA, TORU; US2001/6969; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 83410-15-5, 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 83410-15-5, name is 4-Chloro-5-iodo-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

10 g (39 mmol) A-3, 4.1 mL (47 mmol) morpholine and 16 g (118 mmol) potassium carbonate are suspended in acetonitrile and stirred at 80 C for three h. The reaction mixture is cooled to RT, filtered and the filtrate is concentrated under reduced pressure. Yield: 12 g (100%).

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 83410-15-5, 4-Chloro-5-iodo-6-methylpyrimidine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (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.51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.559, as common compound, the synthetic route is as follows.Recommanded Product: 4-Chloro-2-methoxypyrimidine

6.01.12.01 4- 2-methoxy-pyrimidin-4-yl)-piperazine-l-carboxylic acid tert-butyl ester 1.3 g piperazine-l-carboxylic acid tert-butyl ester and 1.42 mL DIPEA were added to 1 g 2,4- dichlor-pyrimidine in 10 mL dichlormethane. The reaction was stirred over night at RT. The solvent was removed and the residue was purified by chromatography on silica gel (cyclohexane/ ethylacetate) to yield 1.6 g of the desired compound. Rt: 2.10 min (method I), (M+H)+: 299

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51421-99-9, 4-Chloro-2-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/107761; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Step 3: Preparation of 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Tetrahydrofuran (5 mL) and N-bromosuccinimide (116 mg) were added to 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg). The mixture was stirred for 1 hr and, upon completion of the reaction, ethyl acetate was added thereto, and washed with water. The mixture was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1 H), 8.71 (s, 1 H), 8.24 (d, 1 H)

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Hanmi Pharmaceutical Co., Ltd.; PARK, Chul Hyun; KIM, Won Jeoung; JUNG, Young Hee; KIM, Nam Du; CHANG, Young Kil; KIM, Maeng Sup; EP2738174; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia