Category: pyrimidines

Electric Literature of 147539-23-9 , The common heterocyclic compound, 147539-23-9, name is 1-Boc-4-(6-Chloro-5-nitro-4-pyrimidinyl)piperazine, molecular formula is C13H18ClN5O4, 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.

61b) 4-[6-(2-Cyano-ethylamino)-5-nitro-pyrimidin-4-yl]piperazine-1-carboxylic acid t-butyl ester; [] 4-(6-Chloro-5-nitro-pyrimidin-4-yl)piperazine-1-carboxylic acid t-butyl ester (3.0 g) was dissolved in acetonitrile (30 mL), and then 3-aminopropionitrile (0.71 mL) and triethylamine (1.58 mL) were added to this solution. After stirring the reaction solution at room temperature for 14 hours, water (60 mL) was added. The reaction solution was stirred at room temperature for 30 minutes, and then the precipitate was collected by filtration. The obtained yellow solid was washed with water and hexane to give the title compound (1.97 g).

The synthetic route of 147539-23-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1568699; (2005); A1;,
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Synthetic Route of 42839-08-7, 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 42839-08-7, name is Ethyl pyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Mg (0.48 g, 20 mmol) was added to a round-bottomed flask dried at room temperature and I2 (0.2 g) and THF (60 mL) were added under a nitrogen stream.After cooling to 01-Bromo-4-chlorobenzene (3.82 g, 20 mmol) was added slowly and the solution was stirred at room temperature for 2 hours.After cooling to 0 Ethyl pyrimidine-2-carboxylate (1.52 g, 10 mmol)Was dissolved in THF (30 mL) and slowly added to the above solution for 1 h and stirred for 2 h.After completion of the reaction, the reaction mixture was extracted with NH4Cl and ethyl acetate. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography (EtOAc / Hexane)The target compound, bis(4-chlorophenyl) (pyrimidin-2-yl) methanol (1.88 g, yield 57%).

According to the analysis of related databases, 42839-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Doosan Co., Ltd; Lee Yong-hwan; Kim Hoe-mun; (62 pag.)KR2019/33218; (2019); A;,
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Reference of 5807-14-7, 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.5807-14-7, name is 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine, molecular formula is C7H13N3, molecular weight is 139.1982, as common compound, the synthetic route is as follows.

[0119] Red solid benzyl potassium (9.6 g, 73.3 mmol) was added into the solution of 1.5.7-triaza[4.4.0]bicyclo-dec-5-ene (10.2 g, 73.3 mmol) in 350 ml of dry toluene at -40 C. The temperature was allowed to warm to room temperature and the mixture stirred for 16 hours. The colour changed via red to a white slurry. The solvents were removed in a vacuum, the product washed with 3×60 ml of ether and dried in a vacuum to obtain 10.1 g (78%) of white powder. 1H-NMR in THF-d8; delta: 3.17 (t, 4H); 2.98 (t, 4H); 1.69 (t, 4H). The potassium salt product could not be analysed with MS. Elemental analysis calc.: C 47.4%, H 6.8%, N 23.7%, K 22.1%. Elemental analysis found: C 46.0%, H 6.4%, N 23.1%.

Statistics shows that 5807-14-7 is playing an increasingly important role. we look forward to future research findings about 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine.

Reference:
Patent; Andell, Ove; Maaranen, Janne; Hoikka, Jouni; Vanne, Tiina; Rautio, Soile; US2003/225275; (2003); A1;,
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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 831203-15-7, name is 2-(5-Bromopyrimidin-2-yl)acetonitrile. This compound has unique chemical properties. The synthetic route is as follows. name: 2-(5-Bromopyrimidin-2-yl)acetonitrile

General procedure: The title compound of this step was prepared by the method described in Example 1, Step 3,2- (5-bromopyrimidin-2-yl) acetonitrile (0.724 g, 3.66 mmol), 4-chloro-2-fluorophenylboronic acid (0.829 g, 4.75 mmol)Potassium carbonate (1.517 g, 10.98 mmol),Tetrakis (triphenylphosphine) palladium (0.338 g, 0.292 mmol)In toluene (15 mL) with nitrogen at 100 C for 15 hours.The crude product was directly purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / V) = 5/1)The compound (orange solid, 563 g, 62.2%)

With the rapid development of chemical substances, we look forward to future research findings about 831203-15-7.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Wei Dehuo; Xue Yaping; Zhang Yingjun; (44 pag.)CN106674207; (2017); A;,
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Related Products of 15846-19-2, 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 15846-19-2 as follows.

Prepared as described for N-cyclohexyl-4-iodopyridin-3-amine (Intermediate 17), to a stirred solution of 4-chloro-6-meth.oxypyrimidin-5-amine (CAS 15846-19-2; 0.15 g, 0.940 mmol) and cyclohexanone (CAS 108-94-1; 0.294 nil, 2.82 mmol) in anhydrous DCM (5 mL) under an atmosphere of nitrogen at 0 C was added T1CI4 solution (lM in DCM, 3.66 mL, 3.66 mmol). The reaction was stirred at room temperature for 2 h. Sodium triacetoxyborohydride (1.94 g, 9.15 mmol) was added portionwise and the reaction stirred at room temperature for 16 h. The crude product was purified by column chromatography (silica, 0-20% EtOAc / petroleum ether) to afford the title compound.MS ES+: 242

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15846-19-2, its application will become more common.

Reference:
Patent; DAVENPORT Richard; DUNN Jonathan; FARNABY William; HANNAH Duncan; HARRISON David; WRIGHT Susanne; WO2015/198046; A1; (2015);,
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Related Products of 74647-39-5, 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 74647-39-5 as follows.

4-phenylpyrimidine-2-carboxylic acid (0.01 mol)Dissolved in 15 mL of thionyl chloride,Reflux reaction 5-7h, evaporated to dryness,The obtained solid was vacuum-dried and stored,To give the intermediate 4-phenylpyrimidine-2-carbonyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74647-39-5, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Gong, Ping; Zhao, Yanfang; Liu, Yaijing; Di, Xin; Tang, Qidong; (42 pag.)CN104072480; (2016); B;,
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Reference of 774549-55-2, 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 774549-55-2 as follows.

EXAMPLES 32-34 Other N-((dimethylamino)methylene)pyrazolo (1,5-a)-pyrimidine-3-carboxamide and N-((dimethylamino) methylene)-4,5-dihydropyrazolo(1,5-a)pyrimidine-3-carboxamide products which are prepared from corresponding pyrazolo(1,5-a)pyrimidine-3-carboxamide or the 4,5-dihydropyrazolo(1,5-a)pyrimidine-3-carboxamide intermediate compounds by heating with N,N-dimethylformamide dimethyl acetal in the manner described in Examples 20-22 are listed in Table IX.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,774549-55-2, its application will become more common.

Reference:
Patent; American Cyanamid Company; US5059691; (1991); A;,
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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. 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H5ClN2O2

Intermediate 1 (300 mg, 1 eq.), phenylboronic acid (296 mg, 1.3 eq.), tetrakis(triphenylphosphine)palladium (108 mg, 0.05 eq.) and 2N aqueous sodium carbonate solution (654ul, 3 eq.) were mixed in 5 ml of glycol dimethyl ether and reacted under microwave at 120 C for 50 min. The mixture was cooled and evaporated to remove solvent. Water was added and the mixture was extracted with dichloromethane twice, rinsed with saturated brine once, dried over sodium sulfate, filtered, and evaporated to remove solvent to give 310 mg of intermediate 23a. MS (ESI): 203(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, 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
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Electric Literature of 60025-06-1, 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 60025-06-1 as follows.

A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanone (3.81 g, 19.9 mmol) in 90 mL of dioxane at 0 0C was treated with triethylamine (2.78 mL, 19.9 mmol) and hydrazine hydrate (1.16 mL, 23.9 mmol). After addition, the reaction was stirred for 18 h at rt. The mixture was filtered and the precipitate washed with dioxane. The combined organics were evaporated and chromatographed on silica gel, eluting with 30-35% ethyl acetate/ hexanes to afford 2.98 g, (89%) of 4-chloro-3-methyl-1 H-pyrazolo[3,4-d]pyrimidine; 1H NMR (500 MHz, DMSO-cfe) delta 8.71 (1H), 2.60 (3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60025-06-1, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2006/90261; (2006); A1;,
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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. 34253-03-7, name is Methyl pyrimidine-2-carboxylate, the common compound, a new synthetic route is introduced below. Product Details of 34253-03-7

Step B: Preparation of pyrimidin-2-ylmethanol: NaBH4 (0.22 g, 5.79 mmol) was added in one portion to a solution of methylpyrimidine-2-carboxlate (0.80, 5.79 mmol) in EtOH (30 mL). The reaction mixture was left at room temperature overnight before carefully quenching with water (5.0 mL) and concentrating to dryness. The residue was taken up in MeOH and filtered. The filtrate was concentrated and was purified by flash column chromatography, eluting with CH2Cl2/MeOH (100:1) to give 0.18 g (28%) of the desired product as a yellow oil. Step B: Pyrimidin-2-ylmethanol: A solution of methyl pyrimidine-2-carboxylate (659 mg, 4.77 mmol, 1.00 equiv) in 25 mL EtOH was cooled to 0 C. in an ice bath, and sodium borohydride (181 mg, 4.77 mmol, 1.00 equiv) was added. The reaction mixture was warmed to ambient temperature, and stirred 2 hours, and then 5 ml water was added. The reaction was concentrated under reduced pressure, and the residue was purified using silica gel chromatography to give the desired product as a white solid (154 mg, 30%).

The synthetic route of 34253-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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