Pyrimidines

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. 36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine, molecular formula is C6H9N3O2, 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. Application In Synthesis of 2-Amino-4,6-dimethoxypyrimidine

In a 3000 liter glass-lined reactor, 2000 kg of metered methylene chloride, 580 kg of [3-(N,N-dimethylaminocarbonyl-2-pyridyl)sulfonylamino]carboxylic acid phenyl ester and 215 kg of pyrimidinamine were added, heated to 40 C (heating rate of 5 C / h), and stirred for 5 hours. Pyrimidineamine was detected by thin layer chromatography, the end point was an unreacted pyrimidine amine with a mass concentration of less than 2%. The developing solvent for thin layer chromatography was a mixed solvent of chloroform and methanol (volume ratio of 2:1). Until the end of the reaction, a solution of 150 kg of sodium carbonate and 400 kg of water were added, stirred, layers were separated, and the aqueous layer were neutralized with hydrochloric acid (30%) to precipitate nicosulfuron crystallization hydrate. The filtrate was cooled to 15 C, filtered (reduced rate was 10 C / h), and the filter cake was dried at 50 C for 4 hours and then sampled and measured. When the material was measured to constant weight and dried, and 543 kg of the finished nicosulfuron crystallization hydrate was obtained, the yield was 95.47%, and the content of the external standard method was 98.11%.

With the rapid development of chemical substances, we look forward to future research findings about 36315-01-2.

Reference:
Patent; Zibo Xin Nongji Crop Science Co., Ltd.; Zheng Youkui; Cui Yuanxing; Shao Changlu; Huang Hua; (11 pag.)CN110330480; (2019); A;,
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Electric Literature of 955368-90-8 , The common heterocyclic compound, 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, molecular formula is C9H10N4OS, 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.

Step-1: Synthesis of 6-(methylthio)-2-propyl-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-allyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-on (2.0 g, 8.9 mmol, 1.0 eq) in dry MeOH (50 mL), Pd/C (10 wt %) (200 mg) was added under stirring under inert atmosphere in Parr vessel. The reaction was stirred in Parr reactor at 60 psi hydrogen pressure 12 h. The reaction was monitored by LCMS. After completion the mixture was filtered through celite and concentrated to afford, 6-(methylthio)-2-propyl-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one as yellow solid (1.318 g, 65%).

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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Synthetic Route of 56844-38-3, 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 56844-38-3 as follows.

EXAMPLE 2 2-Chloro-5-Methyl-4-(3,4-Methylenedioxybenzylamino)-Thieno-[2,3-d]-Pyrimidine Following the procedure of Example 1, the reaction of 3,4-methylenedioxybenzylamine with 2,4-dichloro-5-methyl-thieno-[2,3-d]-pyrimidine gives 2-chloro-5-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56844-38-3, its application will become more common.

Reference:
Patent; Cell Pathways, Inc.; US6133271; (2000); A;; ; Patent; Cell Pathways, Inc.; US5948911; (1999); A;,
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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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 62802-42-0

(3S,5S)-1-(5-Fluoropyrimidin-2-yl)-5-hydroxypiperidine-3-sulfonamide and (3S,5R)-1-(5-fluoropyrimidin-2-yl)-5-hydroxypiperidine-3-sulfonamide and (3R,5S)-1-(5-fluoropyrimidin-2-yl)-5-hydroxypiperidine-3-sulfonamide and (3R,5R)-1-(5-fluoropyrimidin-2-yl)-5-hydroxypiperidine-3-sulfonamide, Example 228.0 (1153) To a 500-mL round-bottomed flask was added Example 228.2 (8.91 g, 37.1 mmol) and Hunig’s base (32.3 mL, 185 mmol) in DMF (80 mL). 2-Chloro-5-fluoro-pyrimidine (18.32 mL, 148 mmol) was then added with stirring. The reaction mixture was stirred at 120 C. for 18 h. LCMS analysis indicated the reaction was complete. The reaction mixture was allowed to cool to RT and then was diluted with water and extracted with DCM. The organic layers were washed with brine and dried over Na2SO4. The solution was then filtered and concentrated in vacuo to give the initial material as an orange oil. The material thus obtained was purified by silica gel chromatography (a gradient of 0-100% EtOAc in DCM), to provide 228.0 (3.7 g, 10.93 mmol, 36% yield) as a light-yellow solid. LCMS-ESI (pos), m/z: 277.0 (M+H)+.

The synthetic route of 62802-42-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); 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. 57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 57489-77-7

To 5f7-dichIoropyrazolo[l,5-a]pyrimidine (7.6 g, 40.4 mmol) in a sealed vessel was added NH4OH (100 mL). The vessel was then sealed and heated at 85C for 2.5 hours, at which time the consistency of the white solid had changed (from foamy white solid to free- flowing white solid). The vessel was removed from the heat source and allowed to cool to room temperature overnight. On cooling, the contents of the vessel were collected and dried by vacuum filtration giving 5-chloropyrazolo[l,5-a]pyrimidin-7-amine as a yellow-tinged white solid (6.8 g, 40.3 mmol, 100%).

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, 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew; WO2012/27234; (2012); A1;,
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Reference of 54326-16-8, 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. 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

EXAMPLE 8 5-Chloro-1-(5-methyl-2-thenoylmethyl)pyrimidin-2-one A mixture of 5-chloropyrimidin-2-one (522 mg) and 2-bromoacetyl-5-methylthiophene (1.30) g) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 2 h. the mixture was concentrated to ca. 10 ml, diluted with ethyl acetate (100 ml), washed with water (*3) and brine, dried (MgSO4) and evaporated to a gum. The gum was triturated with diethyl ether and the resulting solid dissolved in ethanol and treated with charcoal. Evaporation of the solvent followed by recrystallisation of the residue twice from ethyl acetate gave the title pyrimidinone (205 mg) m.p. 199-203 C., epsilonmax (EtOH) 226.5 nm (epsilon8,570), 261.5 nm (epsilon9,280), 297 nm (epsilon11,630).

According to the analysis of related databases, 54326-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; US4650800; (1987); A;,
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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.42839-09-8, name is 2-Pyrimidinemethanol, molecular formula is C5H6N2O, molecular weight is 110.11, as common compound, the synthetic route is as follows.Product Details of 42839-09-8

Preparation of i-2a; Step A: Preparation of pyrimidin-2-ylmethyl methanesulfonate (i-2a); Methanesulfonyl chloride (4.40 mL, 57.1 mmol) was added to a stirred solution of2-hydroxymethylpyrimidine (6.28 g, 57.1 mmol) and triethylamine (9.50 mL, 68.5 mmol) in DCM (250 mL) at 00C. After approximately 20 min, the reaction mixture was poured into water, the organic layer was separated and the aqueous phase was re-extracted twice with DCM. The combined organic extracts were washed with water, brine, dried (sodium sulfate), and concentrated in vacuo to afford the title compound i-2a. 1HNMR (500 MHz, CDCl3): delta 8.81 (d,2H, J= 4.8 Hz), 7.32 (t, IH, J= 4.9 Hz), 5.46 (s, 2H), 3.24 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42839-09-8, 2-Pyrimidinemethanol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2007/120574; (2007); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 3934-20-1 , The common heterocyclic compound, 3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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 mixture of 2,4-dichloropyrimidine (50g, 336mmol), tert-butyl 4-methylpiperazine-1-carboxylate (67.2g, 336mmol), and toluene (500mL) was stirred at 110 C overnight. The mixture was poured into water, and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (109g, 73%) as a colorless powder. 1H NMR (300MHz, CDCl3) delta: 1.49 (9H, s), 3.44-3.53 (4H, m), 3.75-3.84 (4H, m), 6.53 (1H, d, J=5.1Hz), 8.16 (1H, d, J=5.1Hz). MS (ESI): m/z 299 [M+H]+.

The synthetic route of 3934-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kono, Mitsunori; Matsumoto, Takahiro; Imaeda, Toshihiro; Kawamura, Toru; Fujimoto, Shinji; Kosugi, Yohei; Odani, Tomoyuki; Shimizu, Yuji; Matsui, Hideki; Shimojo, Masato; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1468 – 1478;,
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Application of 175791-49-8 , The common heterocyclic compound, 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4BrN3, 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.

To a solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (1, 0.9 g, 4.54 mmol) in tetrahydrofuran (10 mL) at 0 C., was added sodium hydride (0.27 g, 6.81 mmol, 60% in hexane). The reaction mixture was allowed to stir at 0 C. for 20 min. Chloromethyl 2-trimethylsilylethyl ether (0.9 g, 5.44 mmol) was then added and the reaction mixture was stirred at 0 C. for an additional 30 min., and then quenched with water. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using 5% methanol in dichloromethane to afford 5-bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (2). Yield: 1.3 g, 86%; MS (ESI) m/z 328[M+1]+.

The synthetic route of 175791-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
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Reference of 4765-77-9, 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 4765-77-9, name is 6-Chloropyrimidin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-chloropyrimidin-4(3H)-one (5 g), methyliodide (2.6 mL) and K2CO3 (10.6 g) in acetone (100 mL) is stirred at room temperature over night. The mixture is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried (MgSO4) and concentrated. The residue is triturated with diisopropylether to give the title compound. Yield: 5.1 g; LC (method 1 1 ): tR = 0.25 min; Mass spectrum (ESI+): m/z = 145 [M+H]+.

According to the analysis of related databases, 4765-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
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