Tag: M.W:100-200

Reference of 22536-66-9, Adding some certain compound to certain chemical reactions, such as: 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide,molecular formula is C5H4ClN3O, 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 22536-66-9.

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17573-78-3, 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.17573-78-3, name is 4,5,6-Trifluoropyrimidine, molecular formula is C4HF3N2, molecular weight is 134.06, as common compound, the synthetic route is as follows.

Example (IV-1) Process e) 2.52 g (0.01 mol) of (5,6-dihydro-[1,4,2]oxathiazin-3-yl)-(2-hydroxyphenyl)-methanone O-methyloxime are dissolved in 10 ml of acetonitrile and admixed with 1.7 g (0.0123 mol) of potassium carbonate. The mixture is then cooled with stirring to 0 C., and 1.34 g (0.01 mol) of 4,5,6-trifluoropyrimidine are then added. Without further cooling, the mixture is stirred for another 12 hours. The solvent is then distilled off under reduced pressure and the residue is poured into water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.3 g (62% of theory) of [2-(5,6-difluoro-pyrimidine-4-yloxy)-phenyl]-(5,6-dihydro-[1,4,2]oxathiazin-3-yl)-methanone O-methyloxime. 1H NMR spectrum (CDCl3/TMS): delta=3.15/3.16/3.17/3.18 (2H); 3.83 (3H); 4.11/4.12/4.13/4.14 (2H); 7.26-7.53 (4H); 8.20 (1H) ppm.

The chemical industry reduces the impact on the environment during synthesis 17573-78-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Aktiengesellschaft; US6407097; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 111196-81-7, name is 2-Chloro-5-ethylpyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-5-ethylpyrimidine

3-Hydroxypropylamine (5.62 mL, 73.5 mmol, 1.2 equiv. ) was dissolved in 250 mL of TMOF/MEOH (1: 5) (TMOF = TRIMETHYL ORTHOFORMATE) and then 2,4- bis (trifluoromethyl) benzaldehyde (14.83g, 61.2 mmol, 1.0 equiv. ) was added to this solution at room temperature with stirring. The resulting solution was stirred at rt for 6 hours and then cooled to 0C. NaBH4 was added to the cooled reaction solution in portions with vigorous stirring. After TLC indicated the reduction complete, the reaction mixture was concentrated under reduced pressure. The residue was diluted with 250 mL of ethyl acetate and washed with water, brine and then dried over NA2SO4. After removal of solvent, 17.1 g (93% yield) colorless oil was obtained as desired N-2,5- bis (trifluoromethyl) benzyl-3-hydroxypropylamine (1C). H NMR (400 MHz, CDCL3), 8 (ppm): 7.9 (s, 1H), 7.75 (M, 2H), 4.0 (s, 2H), 3.8 (t, 2H), 2.85 (t, 2H), 1.76 (M, 2H). To a high pressure flask was added intermediate (1C) (12.23g, 40.6 mmol, 1.0 equiv. ), 2-chloro-5-ethylpyrimidine (4.9 mL, 40.6 mmol, 1.0 equiv. ), triethylamine (11.3 mL, 81.2 mmol, 2.0 equiv. ) and 50 mL of toluene. After the flask was sealed, it was heated to 180C with stirring. After reaction at same temperature for 48 hours, the reaction mixture was cooled to room temperature and then diluted with 100 mL of ethyl acetate. The resulting solution was washed with water, brine and the dried over NA2S04.- After removal of solvent, the residue was purified by chromatography to give 7.7 g (46% yield) of product (LE) as bright brown SOLID. H NMR (400 MHz, CDC13), 8 (ppm): 8. 15 (s, 2H), 7.90 (s, 1H), 7.67 (d, 1H) 9 7.30 (d, 1H), 5.02 (s, 2H), 3.71 (m, 2H), 3.53 (m, 2H), 2.42 (Q, 2H), 1.75 (M, 2H), 1.15 (T, 3H).

The synthetic route of 111196-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2004/92130; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 18740-38-0, 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 18740-38-0 as follows.

EXAMPLE 402,4-Dichlorothieno[2,3-d]pyrimidine; The dione of Example 39 (2.6 g) was placed into a pressure vessel with phosphorus oxychloride (15 mL). The mixture was heated at 200 0C for 2.3 hours and then cooled to room temperature and concentrated under reduced pressure. Residual phosphorus oxychloride was azeotroped . twice with toluene (30 mL) under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The resulting layers were separated and the organic layer was filtered through anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to give 1.06 g of the title compound: MS (ESI+) for C6H2N2CI2S m/z205.0 (M+H)+. 1H NMR (400 MHz, CDCI3) delta 7.42 (d,1 H), 7.61 (d,1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18740-38-0, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/79916; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 51421-99-9, 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.51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.559, as common compound, the synthetic route is as follows.

To a stirred solution of 4-chloro-2-methoxypyrimidine (5.7 g, 39.4 mmol) in EtOH (100 mL)under Ar was added hydrazine hydrate (3.83 mL, 79 mmol) and the reaction mixture washeated up and stirred at 85C for 1 hr. Volatiles were removed under reduced pressure and the resulting crude material was purified by silica gel column chromatography (CH2CI2/MeOH/1- 5%/NH3 1%) to afford the title product (4.40 g, 31.4 mmol, 80% yield) as white solid. ESl-MS:141 [M+H] (LC-MS 2); R = 0.47 (CH2CI2/MeOH 9:1).

The chemical industry reduces the impact on the environment during synthesis 51421-99-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 19810-79-8, 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. 19810-79-8, name is 2-Morpholinopyrimidin-4-ol, molecular formula is C8H11N3O2, 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.

2c) 4- (4-BROMO-PVRIMIDIN-2-VL)-MORPHOLINE A mixture of 2-morpholin-4-yl-pyrimidin-4-ol (6.08 g, 33.6 MMOL) and phosphorus OXYBROMIDE (12.5 g, 43.7 MMOL) in 330 mL MECN is heated to reflux for 1 hour. The reaction is cooled to room temperature, concentrated to half volume, and poured over ice. The resulting mixture is neutralized with a saturated solution of NaHCOs, and then extracted with methylene chloride. The organic phase is washed with saturated NACI (aqueous), dried over ANHYDROUS MGS04, FILTERED, concentrated and dried to an off-white solid (7.11 g, 87%). M+H’= 245.97. H NMR (CDC13) ; a 8.05 (d, 1H), 6.70 (d, 1H), 3.75 (m, 8H).

According to the analysis of related databases, 19810-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 23906-13-0, Adding some certain compound to certain chemical reactions, such as: 23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine,molecular formula is C6H10N4, 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 23906-13-0.

General procedure: An ethanolic solution (25 mL) of 2-hydrazino-4,6-dimethylpyrimidine 1 (0.27 g, 2 mmol) and trifluoromethyl-bdiketones 2a-c (2 mmol) was refluxed for 7 h. The reaction was monitored by tlc. On completion of reaction, solvent was evaporated in vacuo and the solid obtained was recrystallized from ethanol. The tlc and 1H NMR of the reaction mixture showed the formation of a single product 3a-c.

According to the analysis of related databases, 23906-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aggarwal, Ranjana; Bansal, Anshul; Rozas, Isabel; Kelly, Brendan; Kaushik, Pawan; Kaushik, Dhirender; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 350 – 357;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24415-66-5, 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 24415-66-5 as follows.

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 228 mg (about 1.5 mmol) of 6-chloroindole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to give about 108 mg of pure product e9 as a yellow solid with a yield of 76%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24415-66-5, its application will become more common.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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.5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.Product Details of 5305-59-9

Reference Example 9 6-Aminopyrimidine-4-carboxylic acid propyl ester A mixture of 6-chloro-4-aminopyrimidine (2.00 g, 15.4 mmol), palladium acetate (361 mg, 1.61 mmol), 1,3-bis(diphenylphosphino)propane (631 mg, 1.52 mmol), and potassium carbonate (2.55 g, 18.5 mmol) in n-propanol (45 mL) and DMF (15 mL) was stirred at 90C under carbon monoxide atmosphere. The mixture was allowed to stand and cool to room temperature, and then filtered through Celite. Aqueous sodium bicarbonate solution was added to the filtrate, which was extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated off in vacuo. The residue was purified by column chromatography on silica gel (chloroform/methanol = 100/1 to 50/1) to give the title compound (1.86 g, 10.3 mmol, yield 67%). 1H-NMR (delta ppm, CDCl3): 8.71 (d, J = 1.2 Hz, 1H), 7.17 (d, J = 1.2 Hz, 1H), 5.16 (br, 2H), 4.35 (t, J = 6.9 Hz, 2H), 1.83 (tq, J = 7.4, 6.9 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5305-59-9, 6-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2070927; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia