Category: pyrimidines

Application of 90213-66-4 ,Some common heterocyclic compound, 90213-66-4, molecular formula is C6H3Cl2N3, 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.

NaH (1.1 equiv) was slowly added at 0C to a 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1 equiv) solution in THF. The reaction mixture was stirred at 0C for 0.5h. p-Toluensulfonyl chloride (1 equiv) was then added and it was stirred at 0C for 4h. The solvent was evaporated to dryness, and the crude product was diluted with H2O and extracted thrice with CH2Cl2. The organic layer was washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to obtain the crude product for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90213-66-4, its application will become more common.

Reference:
Article; Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; Wu, Tianxiao; Guo, Jing; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
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Reference of 1004-39-3, 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. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol. A new synthetic method of this compound is introduced below.

To a suspension of commercially available 4,6-diaminopyrimidine-2-thiol (5g, 35mmol) in methanol (7OmL) is added IN sodium hydroxide (35mL). The resulting solution is stirred for Ih at rt then evaporated to give a tan solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1004-39-3, 4,6-Diaminopyrimidine-2-thiol, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/22185; (2009); A2;,
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Related Products of 61727-33-1, 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 61727-33-1 as follows.

(0234) To a solution of 5-chloro-2-(methylthio)pyrimidine-4-carboxylic acid (1.026 g, 5.02 mmol) in 1:1 DCM:methanol was added a solution of trimethylsilyldiazomethane (2M/hexanes, 1.6 mL, 3.2 mmol). The reaction was stirred at RT for 30 min and then concentrated to give the desired 29-1, which was used without further purification. MS (ESI): mass calcd. for C7H7ClN2O2S, 218.0; m/z found 219.1 [M]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61727-33-1, its application will become more common.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; HANSEN, Stig; ERLANSON, Dan; CANCILLA, Mark; EP2257637; (2015); B1;,
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Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-Chloro-5-iodopyrimidine, 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 63558-65-6, blongs to pyrimidines compound. Product Details of 63558-65-6

To a vial containing a solution of 4-chloro-5-iodopyrimidine (0.200 g, 0.832 mmol) in DMF (1.333 mL) was added morpholine (0.291 mL, 3.33 mmol) followed by cesium carbonate (0.542 g, 1.664 mmol). The vial was sealed with a Teflon cap and heated at 90C for 80 min, then allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2CI2. The filtrate was concentrated, then further dried under high vacuum.Intermediate 105A: MS (ESI) : m/z = 292.0 [M+H]+ HPLC Peak ret. T = 1.23 minutes was product. (HPLC conditions: Column:Luna C18 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
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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.1260088-72-9, name is 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, molecular formula is C8H8Cl2N2O, molecular weight is 219.0679, as common compound, the synthetic route is as follows.Safety of 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine

General procedure: A mixture of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine7 (257mg, 1.173 mmol), 1H-pyrazolo[4,3-c]pyridin-3-amine (291 mg, 1.735 mmol), N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and N,N-dimethylformamide (4.0 mL) was heated at 70 C for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2x) and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 silica, solvent gradient: 0-100% ethyl acetate in dichloromethane followed by 10% methanol indichloromethane) to yield 176.7 mg of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1260088-72-9, 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Hanan, Emily J.; Baumgardner, Matt; Bryan, Marian C.; Chen, Yuan; Eigenbrot, Charles; Fan, Peter; Gu, Xiao-Hui; La, Hank; Malek, Shiva; Purkey, Hans E.; Schaefer, Gabriele; Schmidt, Stephen; Sideris, Steve; Yen, Ivana; Yu, Christine; Heffron, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 534 – 539;,
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Adding a certain compound to certain chemical reactions, such as: 1514-96-1, 4-Chloro-2-(trifluoromethyl)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, 1514-96-1, blongs to pyrimidines compound. Formula: C5H2ClF3N2

a mixture of (S)-2-amino-4-((2,2-difluoroethyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid (160 mg, 432 mumol) and 4-chloro-2-(trifluoromethyl)pyrimidine (87 mg, 475 mol) in THF (2 mL), H2O (0.5 mL) was added NaHCO3 (73 mg, 864 mumol) and the resulting mixture was stirred at 70 C. for 1 h and then allowed to cool to rt and concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=517.2. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.29 (br d, J=6.39 Hz, 1H) 7.60 (d, J=7.50 Hz, 1H) 6.98-7.09 (m, 1H) 6.31-6.70 (m, 2H) 4.85-4.91 (m, 1H) 3.83 (td, J=14.94, 3.20 Hz, 2H) 3.36-3.64 (m, 6H) 2.76-2.85 (m, 4H) 2.49-2.62 (m, 1H) 2.33-2.46 (m, 1H) 1.75-1.99 (m, 6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1514-96-1, its application will become more common.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
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Synthetic Route of 939986-65-9, 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. 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile. A new synthetic method of this compound is introduced below.

[0202] To a mixture of (4-(5-Ethyl-l,2,4-oxadiazol-3-yl)phenyl)methanamine (50 mg, 0.25 mmol, 1.0 equiv) and IPA (3 mL) in a microwave vial were added 6-chloropyrimidine- 4-carbonitrile (41 mg, 0.30 mmol, 1.2 equiv) and DIPEA (103 uL, 0.59 mmol, 2.4 equiv). The vial was sealed and heated at 160 C in a microwave reactor for 90 min. The mixture was concentrated and purified by RP-HPLC (Phenomenex, gemini 5u C18 150 x 21.2 mm, 10-100% ACN/water both with 0.1% formic acid gradient over 40 min) to provide 23 mg (31%) of 6-((4-(5-ethyl-l,2,4-oxadiazol-3-yl)benzyl)amino)pyrimidine-4-carbonitrile as a white solid. LRMS (ES) m/z 307.2 (M+H). 1 H-NMR (Methanol-^, 400 MHz, ppm) d 8.49 (s, 1H), 8.02 (d, J = 7.9 Hz, 2H), 7.49 (d, J = 7.8 Hz, 2H), 6.96 (s, 1H), 4.72 (s, 2H), 3.10- 2.88 (m, 2H), 1.43 (t, 7 = 7.6 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,939986-65-9, 6-Chloropyrimidine-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CYTOKINETICS, INC.; MORGAN, Bradley P.; VANDERWAL, Mark; CHUANG, Chihyuan; (0 pag.)WO2020/5888; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 611-08-5, 5-Nitrouracil, 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, Computed Properties of C4H3N3O4, blongs to pyrimidines compound. Computed Properties of C4H3N3O4

General procedure: A solution of 8AQ (1 mmol) dissolved in 70C methanol(30 mL) was added a solution of metal salts (1 mmol in 2mL methanol), and then heated for 45 min. Subsequently, asolution of 5Iu or 5Nu (1 mmol in 2 mL methanol) wasadded to the reaction mixture and heated for another 1 h.The formed solid product was collected by filtration, washed3-4 times with cold MeOH and dried under reduced preesureat room temperature

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Article; Pingaew, Ratchanok; Worachartcheewan, Apilak; Prachayasittikul, Veda; Prachayasittikul, Supaluk; Ruchirawat, Somsak; Prachayasittikul, Virapong; Letters in drug design and discovery; vol. 10; 9; (2013); p. 859 – 864;,
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Related Products of 873-83-6, Adding some certain compound to certain chemical reactions, such as: 873-83-6, name is 6-Aminopyrimidine-2,4(1H,3H)-dione,molecular formula is C4H5N3O2, 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 873-83-6.

General procedure: In a reaction vessel, a mixture of 6-aminouracil (2 mmol),aldehyde (1 mmol), and SBA-15-SO3H (0.05 g) was heatedat 120 C under solvent-free conditions for a specified time(completion of the reaction was monitored by TLC). Aftercompletion of the reaction, hot DMF (5 mL) was added andthe catalyst was separated by simple filtration. Then water(15 mL) was added to the filtrate to give the solid product.

According to the analysis of related databases, 873-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rostamizadeh, Shahnaz; Tahershamsi, Leili; Zekri, Negar; Journal of the Iranian Chemical Society; vol. 12; 8; (2015); p. 1381 – 1389;,
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Electric Literature of 1193-21-1, 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.1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, molecular weight is 148.9781, as common compound, the synthetic route is as follows.

To a solution of 4, 6-dichloro-pyrimidine (10.0 g) in THF (10 mL) were added iPr2NEt (10.4 g) and 50% aqueous MezNH (6.05 g). The mixture was stirred at ambient temperature for 28 hr and poured into saturated aqueous NaHCO3. The aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. The residue was suspended in Et20. The precipitate was collected by filtration, washed with Et2O and dried under reduced pressure to give (6-chloro-pyrimidin-4-yl) -dimethyl-amine (6.37 g). ESI MS m/e 157, M ; IH NMR (300 MHz, CDC13) 6 3.12 (s, 6 H), 6.41 (s, 1 H), 8.37 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 1193-21-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
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