Pyrimidines

3680-71-5 , The common heterocyclic compound, 3680-71-5, name is 1,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, molecular formula is C6H5N3O, 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.

18D. 4-Chloro-7H-pyrrolor2,3-d]pyrimidine; To 7W-pyrrolo[2,3-cfjpyrimidin-4-ol (0.425 g, 3.14 mmol) was added phosphorus oxychloride (4 ml). The mixture was heated at reflux for 90 minutes and then cooled to room temperature. The solution was poured onto cracked ice, and extracted with chloroform (3 x 50 ml) and ethyl acetate (100 ml). The extracts were then dried and concentrated, and the residue obtained triturated with hot ethyl acetate (200 ml) to yield the desired product (0.204 g, 42percent).

According to the analysis of related databases, 3680-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2007/125315; (2007); A2;,
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611-08-5 , The common heterocyclic compound, 611-08-5, name is 5-Nitrouracil, molecular formula is C4H3N3O4, 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.

A suspension of 5-nitrouracil (10 g, 63 mmol) in POCl3 (100 mL) was refluxed for 5 h in the presence of N,N-dimethylaniline (10 mL), cooled to room temperature and poured on to crushed ice with vigorous stirring. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was evaporated under reduce pressure. The residue was purified by chromatography on silica gel (hexane/ethyl acetate; 1/1; v/v) to give the desired 2,4-dichloro-5-nitropyrimidine. LCMS: ret. time: 23.26 min.; purity: 95percent; 1H NMR (CDCl3): delta 9.16 (1H, s).

According to the analysis of related databases, 611-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, 32779-36-5, blongs to pyrimidines compound. 32779-36-5

To a solution of 5-bromo-2-chloro-pyrimidine (0.5 g, 2.58 mmol) in 1,4-dioxane (20 mL),tert-butyl piperazine-1-carboxylate (0.722 g, 3.88 mmol) and K2C03 (0.713 g, 5.17 mmol)were added at RT. The reaction mixture was refluxed for 4 h (TLC indicated complete consumption of starting material). The reaction mixture was brought toRT, diluted withwater (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic extracts werewashed with water (2 x 40 mL), brine (1 x 40 mL), dried over Na2S04 and concentratedunder reduced pressure to give the residue. The residue was further purified by columnchromatography (100-200 silica gel, 15 g, 10% EtOAc-Hexane) to afford tert-butyl4-(5-bromopyrimidin-2-yl)piperazine-l-carboxylate (0.7 g, 78%) as a white solid.1H NMR [400 MHz, CDCh]: J 8.29 (s, 2H), 3.75 (t, J = 4.8 Hz, 4H), 3.47 (t, J = 5.2 Hz,4H), 1.47 (s, 9H).LCMS: m/z: 287.44 [M-tBut.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-36-5, its application will become more common.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 3740-92-9

3.77g ((4-(5H-benzofuro[3,2-c]carbazol-5-yl)phenyl)boronic acid) (10mmol, 1eq) with 9g (22mmol, 4eq)4,6-Dichloro-2phenylpyrimidine, N2 was exchanged three times, and 0.16 g (0.1 mmol, 1percent eq) of tetrakistriphenylphosphine palladium was added under the protection of N2.2M K2CO3 aqueous solution, ethanol, toluene (volume ratio = 1:2:1), a total of 100ml in an anaerobic environment for 12h,The ethanol and toluene were distilled off under reduced pressure, dissolved in dichloromethane, and the organic phase was washed with water.The filtrate was subjected to column chromatography to obtain 3.12 g of (5-(4-(6-chloro-2-phenylpyrimidin-4-yl)phenyl)-5H-benzofuro[3,2-c]carbazole) (60percent);

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, 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Patent; Huazhong University of Science and Technology; Wang Lei; Zhang Qing; Zhuang Shaoqing; (40 pag.)CN108285452; (2018); A;,
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3934-20-1, 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 3934-20-1 as follows.

A solution of 2,4-dichloropyrimidine (0.500g, 3.36mmol) and N,N-diisopropylethylamine (0.818mL, 4.70mmol) in isopropanol (5mL) was stirred at 0C. Morpholine (0.319mL, 3.69mmol) was added dropwise and the solution continued to stir at 0C for 30min, and then room temperature for 12h. The reaction mixture was concentrated under reduced pressure and then partitioned between ethyl acetate and water. The organic layer was extracted three times, washed with brine, dried over sodium sulfate, and concentrated to dryness. The products were purified by silica column chromatography in hexanes and ethyl acetate to afford 4-(4-chloropyrimidin-2-yl)morpholine and 4-(2-chloropyrimidin-4-yl)morpholine in 7% and 92% yields, respectively. (0058) 4-(4-chloropyrimidin-2-yl)morpholine (15). (White solid, Yield: 7%). 1H NMR (500MHz, CDCl3) delta ppm 3.74 (m, 4H), 3.81 (m, 4H), 6.53 (d, J=4.9Hz, 1H), 8.16 (d, J=4.9Hz, 1H). LCMS found 200.0, [M+H]+. (0059) 4-(2-chloropyrimidin-4-yl)morpholine (16). (White solid, Yield: 92%). 1H NMR (500MHz, CDCl3) delta ppm 3.64 (br. s, 4H), 3.77 (m, 4H), 6.38 (d, J=5.9Hz, 1H), 8.07 (d, J=6.3Hz, 1H). LCMS found 200.0, [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Woodring, Jennifer L.; Bachovchin, Kelly A.; Brady, Kimberly G.; Gallerstein, Mitchell F.; Erath, Jessey; Tanghe, Scott; Leed, Susan E.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Sciotti, Richard J.; Pollastri, Michael P.; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 446 – 459;,
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Adding a certain compound to certain chemical reactions, such as: 461-98-3, 2,6-Dimethylpyrimidin-4-amine, 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, 461-98-3, blongs to pyrimidines compound. 461-98-3

To a 200 ml flask was added 4-amino-2-chloro-5-nitropyridine (1.00 g, 5.76 mmol), 4-amino-2,6-dimethylpyrimidine (1.42 g, 11.5 mmol), Pd2(dba)3 (0.528 g, 0.576 mmol), XantPhos (0.400 g, 0.691 mmol), Cs2CO3 (4.13 g, 12.7 mmol) and dioxane (45 mL). The mixture was degassed with N2 for 2 min and then heated at 110 C. for 16 hrs. After cooling to room temperature the reaction was filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane) to give N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, yield: 23%). LCMS (ESI) m/z: 261.2 [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,461-98-3, its application will become more common.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
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672-45-7, 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 672-45-7, name is 2,4-Dihydroxy-6-trifluoromethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 18. 6-Trifluoromethyl-1-(2-trimethylsilyl)ethoxymethylpyrimidine-2,4-dione In a similar manner to the procedures described in Reference Example 3, reactions were carried out using 6-trifluoromethylpyrimidine-2,4-dione, instead of pyrimidine-2,4-dione,and using 2-(trimethylsilyl)ethoxymethyl chloride, instead of benzyloxymethyl chloride, to give the title compound (yield 48%) as a colorless oil. 1H-Nuclear magnetic resonance spectrum (270 MHz, CDCl3) delta ppm: 8.84 (1H, br.s), 6.24 (1H, d, J=2Hz), 5.32 (2H, s), 3.73-3.68 (2H, m), 0.97-0.90 (2H, m), 0.01 (9H, s).

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 672-45-7, 2,4-Dihydroxy-6-trifluoromethylpyrimidine.

Reference:
Patent; Sankyo Company Limited; EP1069110; (2001); A1;,
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302964-08-5, 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 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

j00557j A solution of 1-(17-azido-3,6,9,12,15-pentaoxaheptadecyl)piperazine (1.50 g,4.00 mmol) in DMF (5 mL) was charged with potassium carbonate (1.10 g, 8.00 mmol) and 2-((6-chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5 -carboxamide (1.58 g, 4.00 mmol). The resulting solution was heated at 100C for 16 h. Thereaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 2% methanol in DCM to obtain 1.20 g, 36% yield of the title compound as an off white solid. ?H NMR (400 MHz, DMSO-d6): oe = 11.44 (s, 1H), 9.86 (s, 1H), 8.21 (s, 1H), 7.40(dd, J= 7.8, 1.9 Hz, 1H), 7.32 – 7.21 (m, 2H), 6.05 (s, 1H), 3.63 -3.54 (m, 27H), 3.42 -3.28 (m, 5H), 2.40 (s, 3H), 2.24 (s, 3H).

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 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
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213265-83-9, Adding some certain compound to certain chemical reactions, such as: 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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 213265-83-9.

Intermediate A35-5 (200mg, 0.92mmol) was dissolved in tetrahydrofuran (10mL), was added 4,6-dichloro-5-fluoropyrimidine (154mg, 0.92mmol),Diisopropylethyl amine (357mg, 2.77mmol), 50 stirred overnight, cooled to room temperature, spin dry solvent, the residue was purified by column chromatography (dichloromethane:Methanol = 50: 1) to give an off-white solid (200mg, 62%). 1HNMR (400MHz, CDCl3) delta8.61 (d, J = 4.8Hz, 1H), 8.56 (s,1H), 8.24 (s, 1H), 7.76 (s, 1H), 7.69 (s, 1H), 7.55 (d, J = 11.6Hz, 1H), 5.78 (s, 1H), 4.84 (d, J = 6.0 hz,2H), 2.65 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 213265-83-9.

Reference:
Patent; Suzhou Yunxuan Pharmaceutical Co., Ltd.; Zhang, Xiaohu; (54 pag.)CN105254613; (2016); A;,
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137281-39-1, 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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, the common compound, a new synthetic route is introduced below.

4- [2- (2-amino-4,7-dihydro-4-oxo-3H-pyrrolo [2,3-d] pyrimidin-5-yl) ethyl] benzoic acid (64.6 g 0.19 mol) Add 1L four-necked flask, add 650ml DMF, stir to dissolve, warm to 50 C, add 0.38molN, N-carbonyldiimidazole, and incubate at 60 C for 2 hours, add L-glutamic acid diethyl ester (0.38mol), and warm to Reaction at 80 C for 3 hours, evaporated to dryness under reduced pressure, added 800ml of dichloromethane to dissolve, poured into a mixed solution of 1600ml pure water and 160ml triethylamine, stirred and separated, separated the organic phase, washed twice with pure water 1600ml ¡Á 2 Dry, evaporate to dryness, add 500ml of absolute ethanol and stir to dissolve. Add 72g of p-toluenesulfonic acid monohydrate and 200ml of absolute ethanol solution dropwise under reflux. After the addition is complete, reflux for 1 hour, cool down and crystallize, suction filter, and dry. 87.2 g of crude product was obtained (molar yield 70.1%, purity 92.3%, impurity V content was 6.52%).Add 87.2g of the above crude product to a three-necked reaction flask, add 350ml of N, N-dimethylformamide, heat to 40-45 C, stir to dissolve, add 700ml of absolute ethanol dropwise after complete dissolution, and slowly precipitate a solid. The temperature was lowered to room temperature, and the mixture was crystallized by stirring for 1-2 hours. The solid was filtered to obtain 69.8 g, and the yield was 80.0%.The above-mentioned refining operation was repeated once to obtain 55.4 g of a solid (purity: 98.2%, impurity V content: 0.07%).

Statistics shows that 137281-39-1 is playing an increasingly important role. we look forward to future research findings about 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zang Chao; (10 pag.)CN110305134; (2019); A;,
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