Pyrimidines

Application of 2927-71-1, 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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

2,4-Dichloro-5-fluoropyrimidine (110 mg, 0.65880 mmol) (represented by formula 1-b), 4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzimidazole (180 mg, 0.5657 mmol), (bis(triphenylphosphine))palladium dichloride (30 mg) were added to 2M sodium carbonate solution (1 mL) and ethylene glycol dimethyl ether (3 mL), and the mixture was stirred under nitrogen atmosphere at 85 C. for 2 hours. After cooling to room temperature, the reaction solution was diluted with 10 mL ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The organic phase was concentrated and recrystallized from acetonitrile, filtered to give compound 6-(2-chloro-5-fluoro-pyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-benzimidazole represented by formula 1-c (135 mg, 0.4183 mmol). LC-MS: m/z: (M+H)+=323.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co., Ltd.; XIA, Guangxin; WANG, Qian; SHI, Chen; ZHAI, Xiong; GE, Hui; LIAO, Xuemei; MAO, Yu; XIANG, Zhixiong; HAN, Yanan; HUO, Guoyong; LIU, Yanjun; (202 pag.)US2019/10153; (2019); A1;,
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Electric Literature of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-2,4-dichloropyrimidine (1.33 g, 10 mmol) and 5-aminoindazole (1.64 g, 10 mmol) were slurried in a solution of sodium acetate (20 mL, 0.1 M buffered to pH 4 with acetic acid). The reaction mixture was then heated to 60-65 C for 16 hours at which point no starting materials remained by t.l.c. The reaction mixture was cooled and the precipitate filtered off washed with water (20 mL), saturated sodium bicarbonate solution (10 mL) and again with water (2×20 mL). The solid was dried under vacuum for 12 hours (2.00 g, 7.6 mmol, 76% Yield). 1H,400MHz, delta (d6-DMSO): 5.68 (3H, br s, NH), 7.52 (2H, s, ArH), 7.61 (IH, s, ArH), 8.05 (IH, s, ArH), 8.06 (IH, s, ArH), 9.09 (IH, s, NH); HPLC: 3.95 min; LRMS: m/z = 261.1 (M+H)

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DCAM PHARMA INC; AJAMI, Alfred, M.; DUNCAN, Kenneth, W.; FANG, Xinqin; WO2011/106168; (2011); 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. 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 4,6-Dichloro-5-methoxypyrimidine

A 500 ml, 4-necked flask equipped with thermometer, mechanical stirrer and condenser with gas inlet was purged with N2 and charged with NaH (4.4 g; 0.1 1 mol) and N,N-dimethylformamide (50 ml). In a separate flask were dissolved 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (18.7 g; 0.1 mol) and 4,6-dichloro-5-methoxy-pyrimidine (17.9 g; 0.1 mol) in DMF (50 ml; 0.5 L/mol). The prepared solution was then added dropwise to the above- mentioned NaH/DMF suspension while maintaining the temperature between – 10 and -5C. The resulting mixture is then stirred for one hour, then allowed to warm up to room temperature and stirred for 17 hours. Water (300 ml; 3 L/mol) was added dropwise while maintaining the temperature between 15-300C by cooling with tap water. Heptane (125 ml; 1.25 L/mol) was added and the resulting mixture was heated up to 55C. The aqueous layer was discarded; the organic layer was cooled down to 200C and stirred for another 3-2Oh. The resulting precipitate was filtered and dried in vacuum (at) 500C for 2Oh to yield the title compound as a residue.

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, 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WELLS, Kenneth M.; FECH, Gary; WU, Wenju; FAWZY, Nagy E.; WO2010/135505; (2010); A2;,
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Electric Literature of 31169-25-2, 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 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were placed in a reaction vessel, to which a dilution of oxalyl chloride (46.4 mL, 0.53 mol) in dichloromethane (150 mL) was then added over about 30 min. Subsequently, 7- bromothieno[3,2-d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added, and heated under reflux for 3 hrs. Thereafter, the reaction mixture was quenched before water was added carefully. The Organic layer thus formed was isolated, while the aqueous layer was extracted with dichloromethane. The organic layers were pooled and dried over anhydrous sodium sulfate, and the dried organic layer was subjected to vacuum filtration and vacuum distillation, followed by desiccation with a nitrogen gas to obtain the desired compound (30.5 g, 85percent). ‘H-NMR^OOMHz, DMSO-d6): delta 9.16(s, 1H), 8.79(s, 1H).

According to the analysis of related databases, 31169-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI PHARM. CO., LTD.; BANG, Keuk Chan; PARK, Chang Hee; CHOI, Jae Yul; KIM, Seo Hee; HAM, Young Jin; WO2014/3483; (2014); A1;,
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Application of 16490-02-1, Adding some certain compound to certain chemical reactions, such as: 16490-02-1, name is Pyrimidine-4,6-dicarboxylic acid,molecular formula is C6H4N2O4, 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 16490-02-1.

Dimethyl pyrimidine-4,6-dicalpharboxylalphate (llalpha)To a heated solution (75C) of 4,6-dimethylpyrimidine (846 mg, 8.00 mmol) and NaOH (211 mg, 5.28 mmol) in water (3 mL) was added a solution OfKMnO4 (5.28 g in 25 mL water) overl5 min. The resulting mixture was stirred at 80C for 3 hrs. The hot solution was filtered hot and manganese dioxide washed with hot water (8 mL). The filtrate and washings were concentrated to 5 mL and acidified with cone. HCl to pH 2-3. After cooling, the precipitation was collected, yielding 591 mg of crude pyridine-4,6-dicarboxylic acid. The diacid was then dissolved in MeOH (15 mL) and cone. H2SO4 (1.5 mL) was added dropwise carefully. The mixture was refluxed for 24 hrs, cooled to room temperature and concentrated in vacuo. The resultant oily residue was neutralised with sat. NaHCO3 and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with H2O (50 mL) and brine (5OmL), dried over Na2SO4, filtered and concentrated. The product was then purified by column chromatography (petroleum ether 40-60 : EtOAc 5 : 5 to 3 :7) yielding 311 mg (20%) of 11 a as a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 16490-02-1, Pyrimidine-4,6-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
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Synthetic Route of 6320-15-6 , The common heterocyclic compound, 6320-15-6, name is 4-Chloro-2,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

The 3,5-dimethylbenzene acetonitrile (725mg, 5mmol) was dissolved in 40ml DMF, underice-cooling conditions , added NaH (120mg, 5mmol). Under the protection of nitrogen gas stirred for 1 hour, the system changed from colorless to red winecolor, afterwards added 2,4-dimethoxy-6-chloropyrimidine (924mg,5mmol). At theroom temperature stirred for 48 h, pass the air into the reaction system and stirringwas continued for 48~72 hours. The reaction was stopped , after the solvent wasdistilled off under reduced pressure added 200ml water to adjust the PH toneutral with hydrochloric acid. Extracted with Ethyl acetate (100ml X 3),combined the organic phases and for drying added Anhydrous sodium sulfate.Purified through column chromatography (petroleum ether / ethyl acetate) to obtaina pale yellow solid. Yield 89%; melting point. 110-112 C

The synthetic route of 6320-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University; LIU, JUNYI; LI, CHAO; WANG, XIAOWEI; ZHANG, ZHILI; GUO, YING; TIAN, CHAO; (12 pag.)CN104119283; (2016); B;,
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Related Products of 58536-46-2, Adding some certain compound to certain chemical reactions, such as: 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine,molecular formula is C22H15BrN2, 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 58536-46-2.

A 250 ml four-necked flask was charged with 0.02 mol of C5 and 0.022 mol of C1 under a nitrogen atmosphere.0.06 mol sodium t-butoxide, 2×10-4 mol Pd2(dba)3 [tris(dibenzylideneacetone) dipalladium], 2×10-4 mol P(t-Bu)3 (tri-tert-butylphosphine), 150ml of toluene, heated to reflux for 24 hours, sampling the plate, the reaction is complete, naturally cooled, filtered, the filtrate is steamed, passed through the silica gel column,The target product was obtained with a purity of 98.5% and a yield of 57.50%.

According to the analysis of related databases, 58536-46-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Ye Zhonghua; Li Chong; Xu Kai; Zhang Xiaoqing; Zhang Zhaochao; (38 pag.)CN108239070; (2018); A;,
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Synthetic Route of 330786-24-8, 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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Intermediate 1 (5g) was dissolved in dry DMF (50 mL) and potassium carbonate (8.8 g) was added. The suspension was stirred at ambient temperature for 2 h. After dropwise addition of Intermediate 2 (9 g) dissolved in DMF (10 mL) the reaction mixture was heated at 80C for 14 h. The organic layer was separated and the water layer extracted with EtOAc (3×20 mL). The organic layers were combined and dried over Na2SC>4. Solvent evaporation at reduced pressure and recrystallization result in 6.3g (80%) tert-butyl-(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo [3,4-d] pyrimidin- 1 -yl]piperidine – 1 -carboxylate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; AZAD PHARMACEUTICAL INGREDIENTS AG; MAIER, Thomas; KARAPETYAN, Inna; ARAKELYAN, Alvard; MARGARYAN, Tamara; SARGSYAN, Vardan; STEPANYAN, Heghine; ABOVYAN, Hermine; GERBER AESCHBACHER, Roman; HAFERKAMP, Sven; (37 pag.)WO2017/137446; (2017); A1;,
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Synthetic Route of 873-83-6 , The common heterocyclic compound, 873-83-6, name is 6-Aminopyrimidine-2,4(1H,3H)-dione, molecular formula is C4H5N3O2, 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.

General procedure: A mixture of aromatic aldehyde (1 mmol), malononitrile (0.66 g, 1 mmol), 6-aminouracil(1 mmol), and KBr (0.1 g, 1 mmol) in EtOH (15 mL) was electrolyzed at 78 °C in an undividedcell equipped with a magnetic stirrer, a platinum anode and a zinc cathode under a constantcurrent density of 5 mA cm-2. The progress of the reaction was monitored by thin layerchromatography. After the electrolysis was finished, the mixture was filtered and the filtercake was washed twice with an ethanol/water (1:1) solution to yield pure products 4a?j.

The synthetic route of 873-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kazemi-Rad, Reyhaneh; Azizian, Javad; Kefayati, Hassan; Journal of the Serbian Chemical Society; vol. 81; 1; (2016); p. 29 – 34;,
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Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, Safety of 2-Chloro-5-methylpyrimidine, blongs to pyrimidines compound. Safety of 2-Chloro-5-methylpyrimidine

[0613] Synthesis of methyl 5-methylpyrimidine-2-carboxylate: Me [0614] To a stirred solution of 2-chloro-5-methylpyrimidine (200 mg, 1.55 mmol) in MeOH: CH3CN (4: 1, 10 mL) under argon atmosphere were added Pd(dppf)Cl2 (227 mg, 0.31 mmol) and triethyl amine (0.45 mL, 3.11 mmol) at RT; heated to 100 C and stirred for 16 h in steel bomb under CO pressure. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 60% EtOAc/ Hexanes to afford 5-methylpyrimidine-2-carboxylate (146 mg, 62%) as brick red solid. [0615] 1H-NMR (CDCls, 400 MHz): delta 8.74 (s, 2H), 4.08 (s, 3H), 2.42 (s, 3H); LC-MS: 81.73%; 153 (M++l); (column: X Bridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 2.10 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: 70% EtOAc/ Hexanes (R 0.2)

The synthetic route of 22536-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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