Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, 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 31737-09-4, blongs to pyrimidines compound. Product Details of 31737-09-4

To a stirred solution of 6-chloro-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3 g, 18.68 mmol, 1 equiv.) and tert-butyl piperazine-1-carboxylate (4.2 g, 22.42 mmol, 1.2 equiv.) in EtOH (60 mL) was added NaHCO3(3.1 g, 37.37 mmol, 2 equiv.) at room temperature. The mixture was stirred at 70 degrees Celsius for 5 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2/ MeOH (15:1 to 10:1) to afford tert-butyl 4-(3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4- yl)piperazine-1-carboxylate(5.38 g, 92.78%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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Pyrimidine – Wikipedia

Reference of 55405-67-9, 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. 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

General procedure: To a solution of 6-bromopyridine-2-carbonitrile (80 mg, 0.44 mmol) and 4-(morpholin-4-yl)-5-(4,4, 5, 5-tetramethyl- 1, 3,2-d ioxaborolan-2-yl )-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) (241 mg, 0.523 mmol) in1,4-dioxane (2.5 mL) and water (0.5 mL) was addedtetrakis(triphenylphosphine)palladium(0) (51 mg, 44 pmol) and sodium carbonate (140 mg, 1.32 mmol). The reaction mixture was heated at 120 C under microwave irradiation for 15 minutes, then diluted with water (30 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentratedin vacuo; purification via preparative thin layer chromatography (Eluent: 1:1 petroleum ether ethyl acetate) afforded the product as a brown oil. Yield: 110 mg, 0.252 mmol, 57%. 1H NMR (400 MHz, CDCl3) 8.52 (s, 1H), 7.84-7.93 (m, 2H), 7.74 (s, 1H), 7.59 (dd, J=7.0, 1.2 Hz, 1H), 5.66 (s, 2H), 3.56-3.65 (m, 6H), 3.34-3.40 (m, 4H), 0.93 (dd, J8.3, 8.0 Hz, 2H), -0.05 (s, 9H).

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 55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; PFIZER INC.; GALATSIS, Paul; HAYWARD, Matthew Merrill; HENDERSON, Jaclyn; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; ZHANG, Lei; WO2014/1973; (2014); A1;,
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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.31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, molecular weight is 160.5584, as common compound, the synthetic route is as follows.Application In Synthesis of 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

6-Chloro-1-methyluracil (250 mg; 1.56 mmol) was dissolved in aniline (500 mg; 5.4 mmol) and stirred at 150 C for 90 min. The solid mixture obtained was washed with ether and methanol and dried. White crystals (304 mg; 90%) were obtained. Mp 308-310 C. 1H NMR (DMSO-d6, 25 C, 500.1 MHz), delta: 3.39 (s, 3H, N-CH3); 4.51 (s, 1H, CH), 7.20-7.27 (m, 3H, Ar-H); 7.36-7.45 (m, 2H, Ar-H); 8.55 (s, 1H, NH);13C NMR (DMSO-d6, 25 C, 125.8 MHz), delta: 25.93, 77.91, 123.06, 125.53, 129.79, 138.92, 151.72, 155.35, 162.95; HR-MS (ESI), calcd for C11H11N3O2 m/z [M+Na]+ = 240.07435, found = 240.07468.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Hartman, Tomas; Herzig, Vladimir; Budesinsky, Milos; Jindrich, Jindrich; Cibulka, Radek; Kraus, Tomas; Tetrahedron Asymmetry; vol. 23; 22-23; (2012); p. 1571 – 1583;,
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Pyrimidine – Wikipedia

Electric Literature of 1060815-89-5, 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. 1060815-89-5, name is 7H-Pyrrolo[2,3-d]pyrimidine-5-carbaldehyde, molecular formula is C7H5N3O, 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 O C solution of 7H-pyrrolo[2,3-djpyrimidine-5-carbaldehyde (5.41 g, 36.8mmol) and cesium carbonate (13.18 g, 40.4 mmol) in DMF (147 ml) was added tert-butyl 2-bromoacetate (5.90 ml, 40.4 mmol). The mixture was allowed to warm up to RT byremoving from ice bath. The reaction was stirred for 2 hs. The reaction was poured ontoice water (500 mL) and EtOAc (300 mL) mixture. The product was extracted in theEtOAc. The layers were separated and the aqueous phase was extracted a second time with EtOAc (2x 150 mL). The combined EtOAc layers were washed with brine. The organic layer was collected and dried over sodium sulfate and concentrated undervacuum. The crude product was purified by silica gel chromatography to get tert-butyl 2-(5-formyl-7H-pyrrolo[2,3-djpyrimidin-7-yl)acetate 6.60 g (69%) as clean product. ESIMS(-): MS m/z 262.0.

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 1060815-89-5, 7H-Pyrrolo[2,3-d]pyrimidine-5-carbaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MILLER, Michael Matthew; ALLEN, Martin Patrick; LI, Ling; BOWSHER, Michael S.; GILLIS, Eric P.; MULL, Eric; ZHAO, Qian; SUN, Li-Qiang; LANGLEY, David R.; SCOLA, Paul Michael; (214 pag.)WO2017/176608; (2017); A1;,
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Pyrimidine – Wikipedia

Application of 5600-21-5 , The common heterocyclic compound, 5600-21-5, name is 4-Chloro-6-methylpyrimidin-2-amine, molecular formula is C5H6ClN3, 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.

Compound 7 (1.5 g, 6.5 mmol) was dissolved in 40 ml of dichloromethane under argon, and aluminum chloride (4.4 g, 32.5 mmol) was slowly added portionwise.Then, pyridine (10.5 ml, 129.8 mmol) was gradually added to the above reaction liquid, and the mixture was heated under reflux in an oil bath at 45 C for 30 hours.The reaction was monitored by TLC until compound 7 was completely reacted.The reaction solution was cooled to room temperature, the pH of the reaction mixture was adjusted to 1 with 6M hydrochloric acid, and dichloromethane was evaporated under reduced pressure.The ether layer was washed with 1 M of dilute hydrochloric acid and saturated brine, and the ether layer was dried over anhydrous sodium sulfate.The crude product was recrystallized from ethyl acetate / n-hexane.1.3 g of solid compound 6, yield 96%.

The synthetic route of 5600-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Wu Yong; Hai Li; Zhang Yong; Cheng Xu; Guo Lingmei; Li Weijian; Zhan Zhen; (11 pag.)CN108191878; (2018); A;,
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Pyrimidine – Wikipedia

Reference of 890094-38-9, 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.890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, molecular formula is C7H9ClN4O2, molecular weight is 216.63, as common compound, the synthetic route is as follows.

4-morpholinophenylamine(3.6g) was added to a solution of Compound 2-3(4.3g) in n-butanol(150ml). The mixture was reacted at 90C for 4 hours, cooled to room temperature, filtered, washed and dried to obtain a red solid(5.3g) in a yield of 74.7%. MS m/z(ESI): 359[M+H]+.

Statistics shows that 890094-38-9 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
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Pyrimidine – Wikipedia

Reference of 13053-88-8, 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. 13053-88-8, name is N-(Pyrimidin-2-yl)acetamide. A new synthetic method of this compound is introduced below.

A solution of 2-acpym (0.0184 g, 0.134 mmol) in CH2Cl2 (5 ml) containing three drops of NEt3 was added to a yellow suspension of 1 (0.0395 g, 0.067 mmol) in CH2Cl2 (10 ml). The yellow solution was stirred for 3 h, filtered and slow evaporation at room temperature gave a yellow precipitate which was recrystallized from CH2Cl2 and MeOH to give a yellow powder (0.041 g, 71%). Anal. Calc. for C17H15ClN4OPd, 47.1, H, 3.5, N, 12.9. Found: C, 47.3, H, 3.4, N, 13.2% IR (KBr) 3330s, 3170s, 3278s, 1649s, 1562s, 460 s cm-1. 1H NMR (dmso-d6) delta 9.42 (d, 1H, J 4.0), 8.66 (d, 1H, J 4.0), 8.57 (s, 1H, NH), 8.47 (s, 1H), 7.84 (dd, 1H, J 7.9, 4.0), 7.67 (d, 1H, J 7.9), 7.47 (d, 1H, J 7.9), 7.19 (dd, 1H, J 4.0, 4.0), 7.13 (dd, 1H, J 7.9, 4.0), 6.97 (dd, 1H, J 7.9, 3.8), 6.78 (dd, 1H, J 4.0, 4.0), 6.31 (d, 1H, J 7.9), 1.63 (s, 3H). Mp 182-184 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13053-88-8, its application will become more common.

Reference:
Article; Al-Jibori, Subhi A.; Gergees, Hayfa M.; Al-Rubaye, Mousa S.; Basak-Modi, Sucharita; Ghosh, Shishir; Schmidt, Harry; Laguna, Mariano; Luquin, M. Asuncion; Hogarth, Graeme; Inorganica Chimica Acta; vol. 450; (2016); p. 50 – 56;,
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Pyrimidine – Wikipedia

Electric Literature of 1993-63-1, 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.1993-63-1, name is 5-Fluoro-2-methoxypyrimidin-4-amine, molecular formula is C5H6FN3O, molecular weight is 143.12, as common compound, the synthetic route is as follows.

1 Added 14.3 g to the reaction device4-amino-5-fluoro-2-methoxypyrimidine (0.10 mol),17.55gIsothiocyanatoFormic acidMethyl ester(0.15mol) and 100gEthyl acetate, stirring and warming to reflux, reaction 18h, unseparated[(2-Methoxy-5-fluoropyrimidin-4-yl)amino]thiocarbonylcarbamate methyl ester.Hydroxylamine hydrochloride aqueous sodium hydroxide solution is added to the reacted material[Contains 13.9g of hydroxylamine hydrochloride (0.20mol), 8g of sodium hydroxide (0.20mol)And 70g of water], after the addition of reflux reaction continued 6h.After the reaction is completed, it is lowered to room temperature (15 to 25C, the same below).Stirring, cooling, suction filtration, washing with water, and drying yield 16.8 g of pale yellow solid5-Methoxy-8-fluoro-[1,2,4]-triazolo[1,5-c]pyrimidin-2-amine,The yield was 91.8%.

Statistics shows that 1993-63-1 is playing an increasingly important role. we look forward to future research findings about 5-Fluoro-2-methoxypyrimidin-4-amine.

Reference:
Patent; Jiangsu Nongyong Hormone Engineering Technology Research Center Co., Ltd.; Nanjing Gaoheng Biological Technology Co., Ltd.; Kong Fanlei; Sun Yonghui; Zhang Yuanyuan; Shi Yueping; Gao Jianhong; (5 pag.)CN107602566; (2018); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 14631-08-4, 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 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6; (2-{4-[2-(Trifluoromethyl)phenoxylpiperidin-l-yl}-9H-purin-8-yl)methanol; Step 1: 2-{4-[2-(Trifluoromethyl)phenoxylpiperidin-l-yl}pyrimidine-4,5-diamine; A mixture of 2-chloropyrimidine-4,5-diamine (200 mg, 1.4 mmol), 4-[2- (trifluoromethyl)phenoxy]piperidine (0.4 mL, 1.6 mmol) and triethylamine (0.58 mL, 4.1 mmol) in 2-methoxyethanol/water (4:1, 2.8 mL) was heated at 13O 0C for 16 h. The solvent was evaporated, diluted with water (5 mL) and extracted three times with EtOAc (5 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent followed by purification by Combiflash (SiO2, 5 % MeOeta/EtOAc) afforded the title compound as a solid. MS (+ESI) m/z 354 (MH+).

According to the analysis of related databases, 14631-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2008/17161; (2008); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 5807-14-7, Adding some certain compound to certain chemical reactions, such as: 5807-14-7, name is 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine,molecular formula is C7H13N3, 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 5807-14-7.

To a solution of 1, 3,6, 7, [8-HEXAHYDRO-2H-PYRIMIDO [1, 2-A] PYRIMIDINE] (5.6 g) in 80 mL of THF was added 3- (perfluorooctyl) propyl iodide (11.8 g) and triethylamine (2.6 mL). The mixture was stirred at [25 C] for 12 h. The precipitate was collected by filtration. The solid was mixed with 50 mL of 30% [NAOH,] extracted with EtOAc. The organic layer was concentrated to give desired product as a semisolid (3.8 g, 32%).

According to the analysis of related databases, 5807-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FLUOROUS TECHNOLOGIES INCORPORATED; WO2004/7407; (2004); A2;,
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Pyrimidine – Wikipedia