Pyrimidines

Application of 934524-10-4, 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 934524-10-4 as follows.

A stirred solution of S-2 (5.00 g, 14.6 mmol) in EtOH (50 mL) taken in a round- bottom flask was charged with DIPEA (5.0 mL, 29.2 mmol) and S-11 (1.74 g, 20.5 mmol) at room temperature. The reaction mixture was heated to 80C for 5 h under nitrogen atmosphere and was concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 0- 50% EtOAc in hexanes as eluent to afford S- 12 (3.80 g, 65%, AMRI lot IN-SKY-C-11) as an off-white solid. The compound was characterized by 1H NMR analysis.1H NMR (400 MHz, CDCl3): delta 8.08 (d, J = 8.36 Hz, 2H), 7.39 (d, J = 4 Hz, 1H), 7.30 (d, J = 8.12 Hz, 2H), 6.43 (d, J = 4 Hz, 1H), 5.25 (d, J = 7.48 Hz, 1H), 3.7 (q, J = 14.44 Hz, 1H), 2.39 (s, 3H), 1.28 (d, J = 6.52 Hz, 3H), 0.91- 0.87 (m, 1H), 0.56- 0.41 (m, 2H), 0.39- 0.24 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); 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.703-95-7, name is 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, molecular formula is C5H3FN2O4, molecular weight is 174.0867, as common compound, the synthetic route is as follows.SDS of cas: 703-95-7

Dissolve 5-fluoroorotic acid (Compound 1) (40g, 0.23mol) in N,N-dimethylformamide (500mL). Slowly add DBU (35.0g, 0.23mol) dropwise, stir at room temperature for 1h, then slowly drop iodomethane (32.0g, 0.23mol), and stir at 60 C for 4h. After the reaction was completed, 100 mL of ice water was added with stirring to precipitate a solid, which was filtered, and the filter cake was washed with water (100 mL x 3) and dried in vacuo to obtain compound 2 (30 g, yield = 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,703-95-7, 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Ruiming Drug Discovery Co., Ltd.; Zhang Fei; Feng Zixia; (33 pag.)CN110950868; (2020); A;,
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Reference of 13036-50-5, 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. 13036-50-5, name is 2-Chloro-4-phenylpyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 2-chloro-4-phenylpyrimidine (71 mg, 0.37 mmol), Intermediate 20 (100 mg, 0.34 mmol) and DIPEA (120 muIota_, 0.68 mmol) in NMP (1 mL) was heated at 130C for 3 hrs. The reaction mixture was allowed to cool to ambient temperature and diluted with water (10 mL). The crude product was extracted into diethyl ether (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on the Biotage Companion (12 g column, 0 to 100% diethyl ether in isohexane) to afford the title compound as a gum (65 mg). LCMS (Method A): Two peaks at 2.45 min and 2.66 min, 451 [M+H]+.1H NMR (400 MHz, DMSO-d6, 374 K) 8.36 (d, 0.8 H), 8.30 (bd, 0.2 H), 8.15-8.07 (m, 1 .6 H), 7.97 (bm, 0.3 H), 7.56-7.46 (m, 3.92 H), 7.46-7.24 (m, 7.38 H), 7.16-7.05 (m, 1.8 H), 6.33 (bs, 1 H), 4.41 (td, 1 H), 3.71 (m, 1 H), 3.50 (m, 1 .1 H), 3.26 (bm, 0.2 H), 2.84 (s, 0.3 H), 2.82 (s, 0.3 H), 2.63 (s, 0.3 H), 2.48 (s, 2.1 H), 1 .82 (bm, 0.7 H), 1.00 (d, 2.5 H), 0.78 (bd, 0.5 H), 0.56 (bs, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-50-5, 2-Chloro-4-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); A1;,
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Reference of 153435-63-3, 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 153435-63-3 as follows.

To a suspension of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D44 (300 mg), CsF (329 mg, 2.166 mmol) and Pd(Ph3P)4 (50.0 mg, 0.043 mmol) in DMF (10 ml) stirred under nitrogen at room temperature was added 2-(tributylstannanyl)pyrimidine (480 mg, 1.299 mmol). The reaction mixture was stirred at 130 C. for 30 minutes at microwave Personal Chemistry. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 saturated solution the combined organic phases were dried to give the crude product which was purified by silica gel chromatography (SNAP KP-NH 55 g; Cy/EtOAc 15 column volumes from 100/0 to 70/30). Collected fractions were evaporated to obtain the title compound D45 (101 mg) as white solid. UPLC (Basic GEN_C): rt=0.56 minutes, peak observed: 230 (M+1). C12H11N3O2 requires 229. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.92 (d, 2H), 8.49 (d, 1H), 7.44-7.63 (m, 2H), 3.75 (s, 3H), 2.57 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); 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. 74840-38-3, name is Ethyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate

Step 2: 5-Bromo-2-(2-methoxy-ethylamino)-pyrimidine-4-carboxylic acid ethyl ester2-Methoxyethylamine (0.278 ml, 3.2 mmol) was added at room temperature to a solution of 5- bromo-2-methanesulfonyl-pyrimidine-4-carboxylic acid ethyl ester (0.2 g, 0.65 mmol) in dichloromethane (5 ml). Stirring was continued at 45 C for 2 hours. The solvent was evaporated and the crude product was purified by silica gel chromatography using an ethyl acetate/heptane eluent to yield the title compound as colorless oil (0.175 g, 89 %).MS: M = 304.2 (M+H)+

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, 74840-38-3, Ethyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; VIEIRA, Eric; WO2011/89132; (2011); A1;,
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Application of 2240-25-7, 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. 2240-25-7, name is 4-Amino-5-bromopyrimidin-2(1H)-one, molecular formula is C4H4BrN3O, 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.

5-bromocytosine (95g, 0.5 mol), saturated sodium carbonate solution 200mL, 100 mL of dioxane was added the reaction flask was cooled to 10-15 °C dropwise loading fluorenylmethoxycarbonyl chloride (155.2g, 0.6mol mixed solu tion) and I00mL dioxane, the addition was complete, the reaction was warmed to room temperature and 3h, filtered, and the filter cake water (50mLX 2) washing and drying to give N- Fmoc-5-bromocytosine (196.7g , 95.4percent).

According to the analysis of related databases, 2240-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Xianfeng Technologies Co., Ltd; CHEN, XIAOPING; YAO, FUYOU; LU, WEI; XIAO, MUJIE; GAO, FEIFEI; (6 pag.)CN103819412; (2016); B;,
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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.163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H5IN4, molecular weight is 260.04, as common compound, the synthetic route is as follows.category: pyrimidines

General procedure: Compound 6 (3.85 mmol), Pd(PPh3)4 (0.077 mmol), CuI (0.77 mmol), AmberliteIR-67, ethynylbenzene or 4-ethylphenylacetylene (4.6 mmol) in 30 mL of THF was heated for 30 min at 120 C in the microwave. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite. The solvent was removed in vacuo, and the crude product was purified by flash column chromatography on silica gel (DCM/MeOH= 30/1) to give compound 7i or 7ii as a yellow solid.19 To a solution of 7i or 7ii (7.16 mmol) in DMF (20 mL) was added potassium carbonate (8.6 mmol) followed by 4-bromo-1-butene (8.6 mmol). After stirring at 30 C for 6 h, EtOAc (300 mL) was then added and the solution was washed three times with water. The combined organic phase was dried over Na2SO4 and concentrated. The residue was subjected to column chromatography on silica gel (DCM/MeOH= 30:1) to give compound 8i (83%) or 8ii (~56% yield over two steps). For 8i: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.51 – 7.49 (m, 2H), 7.43 – 7.33 (m, 3H), 7.22 (s, 1H), 5.90 (s, 2H), 5.79 – 5.72 (m, 1H), 5.08 (t, J = 16.2, 10.8 Hz, 2H), 4.26 (t, J = 7.2 Hz, 2H), 2.60 (q, J = 6.9 Hz, 2H); For 8ii: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.43 (d, J = 7.8 Hz, 2H), 7.20 – 7.18 (m, 3H), 5.92 (s, 2H), 5.82 – 5.73 (m, 1H), 5.17 (t, J =17.1, 9.9 Hz, 2H), 4.24 (t, J = 6.9 Hz, 2H), 2.75 – 2.52 (m, 4H), 1.24 (t, J = 7.5 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,163622-50-2, 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Wang, Chengyan; Liu, Hongchun; Song, Zilan; Ji, Yinchun; Xing, Li; Peng, Xia; Wang, Xisheng; Ai, Jing; Geng, Meiyu; Zhang, Ao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2544 – 2548;,
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Synthetic Route of 1231930-42-9, 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. 1231930-42-9, name is 6-(2-Chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C15H13ClF2N4, 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.

110 mg of 2-methoxy-4-(4-tert-butoxycarbonylpiperazin-1-yl)-5-nitroaniline under nitrogen,103 mg of 6-(2-chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 88 mg of Pd2 (dba)3 ,80 mg of BINAP and 203 mg of Cs2CO3 were dissolved in 20 ml of 1,4-dioxane, and the mixture was heated at 140 C for 3 h.The insoluble matter in the reaction liquid was cooled and filtered, and the filter cake was washed with dichloromethane, and the filtrate was evaporated to dryness under reduced pressure.5-Fly-4-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(2-methoxy-4-(4) – tert-Butoxycarbonylpiperazin-1-yl)-5-nitrophenyl)pyrimidin-2-amine 240 mg as a tan solid.

According to the analysis of related databases, 1231930-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); A;,
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Related Products of 6299-25-8, 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 6299-25-8 as follows.

LDA (2M in THF/n-heptane/ethylbenzene) (3.72 ml_, 28.2 mmol) was added dropwise to a solution of commercially available 4,6-dichloro-2-methylsulfanyl-pyrimidine (5 g, 25.63 mmol) in anhydrous THF (30 ml_) at -78 C under a nitrogen atmosphere and the mixture stirred for 1 hour. Ethyl chloroformate (2.7 ml_, 28.24 mmol) was added via syringe and the mixture stirred at -78 C for a further 2 hours and then allowed to warm to room temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride solution (50 ml_) and extracted with EtOAc (2 x 50 ml_). The combined organic portions were dried over MgSCU and the solvent removed in vacuo. Purification by column chromatography on silica eluting with a gradient of 1 to 2% EtOAc in petrol afforded the titled compound as a yellow solid. (1376) LC-MS (Method 3B): Rt 2.52 mins; MS m/z N/A [does not ionise] (1377) 1 H NMR (500 MHz, Chloroform-d) d 4.45 (q, J = 7.1 Hz, 2H), 2.58 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-25-8, its application will become more common.

Reference:
Patent; ADORX THERAPEUTICS LIMITED; MCCARTHY, Clive; MACLEOD, Calum; MOULTON, Ben; LENAGH-SNOW, Gabriel; (190 pag.)WO2019/122932; (2019); A1;,
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Reference of 696-07-1, 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. 696-07-1, name is 5-Iodouracil. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 5-iodopyrimidine (0.84 mmol) in anhydrous DMF (7 mL) were added the terminal alkyne (2.5 mmol), Pd(PPh3)4 (0.08 mmol), CuI (0.08 mmol) and Et3N [or (iPr)2EtN] (1.68 mmol). Method A: The reaction mixture was stirred at room temperature overnight. The extent of the reaction was monitored by TLC and the solvent was evaporated in vacuo and the residue purified by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) to afford 1-10a and 1-6b. Method B: The synthesis was carried out at 50 C for 30 min under microwave irradiation (300 W, 1 bar, Milestone start S microwave oven). Purification by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) afforded compounds 1-10a and 1-6b.

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:
Article; Kraljevi?, Tatjana Gazivoda; Bistrovi?, Andrea; Dedi?, Matea; Paveli?, Sandra Kraljevi?; Sedi?, Mirela; Rai?-Mali?, Silvana; Tetrahedron Letters; vol. 53; 38; (2012); p. 5144 – 5147;,
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