Pyrimidines

Application of 1514-96-1, Adding some certain compound to certain chemical reactions, such as: 1514-96-1, name is 4-Chloro-2-(trifluoromethyl)pyrimidine,molecular formula is C5H2ClF3N2, 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 1514-96-1.

(S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid acetate (100 mg, 228 mumol) in 4:1 THF/H2O (2.5 mL) was added NaHCO3 (57 mg, 684 mumol) followed by 4-chloro-2-(trifluoromethyl)pyrimidine (44 mg, 239 mumol). The resulting mixture was stirred at 70 C. for 1 h and then allowed to cool to rt. The mixture was adjusted to pH=6 by the addition of aq. 1 M HCl and then concentrated in vacuo. The resulting crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=525.3 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.27 (br d, J=5.51 Hz, 1H) 7.60 (d, J=7.28 Hz, 1H) 6.96 (d, J=6.39 Hz, 1H) 6.65 (d, J=7.28 Hz, 1H) 4.86 (br s, 1H) 3.82 (br d, J=5.95 Hz, 1H) 3.42-3.55 (m, 3H) 3.37 (d, J=8.38 Hz, 4H) 3.12-3.30 (m, 4H) 2.72-2.86 (m, 4H) 2.48 (dt, J=11.85, 5.87 Hz, 1H) 2.26-2.39 (m, 1H) 1.95 (q, J=5.90 Hz, 2H) 1.73-1.90 (m, 4H) 1.22 (dd, J=6.06, 1.87 Hz, 3H).

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. 1514-96-1, 4-Chloro-2-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1013916-37-4, 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. 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C13H14ClN3O, 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.

2-Chloro-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (105) (20 g, 76 mmol, 1.0 eq) was dissolved in 250 mL of trifluoroacetic acid and 10 mL of trifluoroacetic anhydride. Under nitrogen protection, N-iodosuccinimide (68.5 g, 304 mmol, 4.0 eq) was added and the mixture was heated to 80 C. After 1 hour, the reaction solution was concentrated in vacuo and sodium bisulfite solution was added to remove the remaining N-iodosuccinimide, extracted with dichloromethane and washed with saturated brine twice. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to obtain compound 2-chloro-8-cyclopentyl-6-iodo-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one as a white solid (29 g, yield: 98.5%). LCMS(ESI): m/z 390[M+1]+.

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 1013916-37-4, 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; GUANGZHOU BEBETTER MEDICINE TECHNOLOGY CO., LTD.; CAI, Xiong; QIAN, Changgeng; LI, Junqi; QING, Yuanhui; WANG, Yanyan; XUE, Weicai; YOU, Huajin; (23 pag.)US2018/297995; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 919116-36-2, name is 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine, molecular formula is C6H4ClF3N2S, 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. name: 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine

To a solution of 3,5-dimethyl-4-(l-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)- 1 //-pyrrolo| 2,3-/;|pyridin-6-yl )isoxazole (9.61 g, 20.1 mmol) in degassed 2:1 mixture of dioxane/water (100 mL) was added CS2CO3 (13.06 g, 40.1 mmol), and obtained suspension was degassed for 30 min. 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine (US20130017194) (5.04 g, 22.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.32 g, 2.01 mmol) were added, and the reaction mixture was stirred at 100 C. After 2 h, another portion of 4-chloro-2- (methylthio)-5-(trifluoromethyl)pyrimidine (1.00 g, 4.38 mmol) was added, and the reaction mixture was heated for another 30 min at 100 C. After cooling down to RT, the mixture was diluted with EtOAc (100 mL) and water (75 mL), and pH was adjusted to pH 8 with sat. aq. NaHC03. Crude product was extracted with EtOAc (3 x 75 mL), combined organic phase was then washed with water (2 x 50 mL) and brine (75 mL), separated, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc in hexanes, 0 to 100% gradient) to provide an orange paste, which was then re-purified by reverse phase chromatography (Cl 8, MeCN in aq. 10 mM ammonium formate pH 3.8, 0 to 100% gradient) to give the title compound as a brown solid (2.05 g, 3.76 mmol, 19% yield).

With the rapid development of chemical substances, we look forward to future research findings about 919116-36-2.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; MARINEAU, Jason J.; CHUAQUI, Claudio; CIBLAT, Stephane; KABRO, Anzhelika; PIRAS, Henri; WHITMORE, Kenneth Matthew; LUND, Kate-Lyn; (200 pag.)WO2019/143719; (2019); A1;,
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.38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile, molecular formula is C5H2FN3, molecular weight is 123.0879, as common compound, the synthetic route is as follows.Product Details of 38275-55-7

To a solution of 5-fluoropyrimidine-2-carbonitrile (Intermediate 1, 1.0 g, 8.1 mmol) in anhydrous THF at -780C was added a solution of DIBAL-H (8.1 mL) over a period of 20 minutes. The resulting mixture was stirred at this temperature for 2hours whereupon MeOH was added. The solution was allowed to warm to room temperature whereupon a solution of concentrated HCl was added. The resulting mixture was stirred for 2 hours at ambient temperature and the aqueous layer was washed with EtOAc (3x). The combined organic extracts were washed with brine and dried (MgSO4). Evaporation of the solvent afforded the titled compound (780 mg, 76%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/117050; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 14161-09-2, name is 2-(Methylsulfonyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 14161-09-2

Example 23 6-Chloro-N-pyrimidin-2-yl-2,3,4,9-tetrahydro-1H-carbazol-1-amine A solution of 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine (50 mg, 0.23 mmol) and 2-methylsulfonylpyrimidine (69 mg, 0.44 mmol) in N,N-dimethylformamide (0.50 mL) was heated at 150 C. for 900 seconds in a Smith Synthesizer microwave. The mixture was diluted with ethyl acetate and extracted with 5% aqueous lithium chloride. The organic layer was isolated and concentrated onto silica. Purification by flash chromatography (0-30% ethyl acetate-hexanes) yielded 6-chloro-N-pyrimidin-2-yl-2,3,4,9-tetrahydro-1H-carbazol-1-amine (8 mg, 12% yield) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 14161-09-2.

Reference:
Patent; Gudmundsson, Kristian; US2009/156621; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 81560-03-4, Adding some certain compound to certain chemical reactions, such as: 81560-03-4, name is 5-Bromo-2-(methylthio)pyrimidin-4(3H)-one,molecular formula is C5H5BrN2OS, 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 81560-03-4.

To a mixture containing 0.70 g (5.5 mmol) of dimethyl sulfate and 0.25 g (4.5 mmol) of potassium hydroxide in 10ml of tetrahydrofuran was added 0.5 g (2.25 mmol) of 5- Bromo-2-(methylthio)pyrirnidin-4(3H)-one in portions over 15 min. After complete addition, the mixture was stirred overnight then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 20 % ethyl acetate/ dichloromethane gave 0.5 g (94 %) of product. ¹H NMR (CDC13) No.: 2.58 (s , 3H) , 3.58 (s, 3H) , 8.06 (s, 1H).

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. 81560-03-4, 5-Bromo-2-(methylthio)pyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/99688; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, 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, 5018-38-2, blongs to pyrimidines compound. category: pyrimidines

Example 8 4-chloro-5,6-dimethoxypyrimidine Following a modified form of the process described by Bretschneider et al., Monatsh Chem. 96 , 1661-1669 (1965), to 6 g (0.11 mol) of sodium methoxide in 150 ml of methanol were added at 0C 17.9 g (0.1 mol) of 4,6-dichloro-5-methoxypyrimidine. The mixture was held at 0C with stirring for 1 hour. It was allowed to rise to room temperature (25C), the salts formed were filtered. The filter liquors were concentrated to dryness. The residue was treated with 100 ml of distilled water and extracted with 3 x 100 ml of CH2Cl2. The extracts were dried and concentrated, thereby yielding 16.1 g of a completely pure white solid. (92.2%). 1H-NMR: (DMSO-d6, ppm): 8.41 (s, 1H); 4.03 (s, 3H) 3.88 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5018-38-2, its application will become more common.

Reference:
Patent; VITA-INVEST, S.A.; EP714896; (1996); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330785-81-4, 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 330785-81-4, name is Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(1) To a suspension of lithium aluminum hydride (4.15 g) in tetrahydrofuran (150 ml) is added a solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (38.32 g) in tetrahydrofuran (100 ml) under ice-cooling at 5 C. to 10 C. over a period of one hour. After the addition, the ice bath is removed, and the reaction mixture is stirred at room temperature for one hour. To the reaction mixture is added water (4.15 ml) under ice-cooling, and thereto is further added 3N aqueous sodium hydroxide solution (4.15 ml). To the mixture is added water (4.15 ml) three times, and the mixture is stirred at room temperature for one hour. The reaction mixture is treated with magnesium sulfate, and the solid precipitates obtained are filtered. The precipitates are washed with tetrahydrofuran. The filtrate and the washings are combined, and concentrated under reduced pressure, and triturated with a mixture of ethyl acetate and isopropyl ether. The resulting crystals are collected by filtration, and washed well with isopropyl ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine as pale yellow crystalline powder. First production: yield; 25.10 g, m.p. 162-163 C. Second production: yield; 2.32 g, m.p. 159-160 C. In addition, the above solid precipitates are washed again with isopropyl ether, and the filtrate is concentrated under reduced pressure to give colorless crystals. The resulting solid is suspended in isopropyl ether, filtered, and the precipitates are washed well with isopropyl ether and hexane to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine (4.26 g) as colorless crystals, m.p. 161-162 C.

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 330785-81-4, Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2003/32647; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7226-23-5 , The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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.

EXAMPLE 61 3-Cyclopentyl-2-(4-methanesulfinyl-phenyl)-N-thiazol-2-yl-propionamide A solution of diisopropylamine (3.2 mL, 23.16 mmol) in dry tetrahydrofuran (10.3 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (3.4 mL) was cooled to -78 C. under nitrogen and then treated with a 10M solution of n-butyllithium in hexanes (2.3 mL, 23.16 mmol). The resulting reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-(methylthio)phenylacetic acid (2.01 g, 11.03 mmol) in dry tetrahydrofuran (10.3 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (3.4 mL). The reaction mixture was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (2.55 g, 12.13 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was stirred at -78 C. for 30 min and then allowed to warm to 25 C. where it was stirred for 24 h. The reaction mixture was quenched with water and then concentrated in vacuo to remove tetrahydrofuran. The remaining aqueous phase was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then extracted with ethyl acetate (1*200 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methylsulfanyl-phenyl)propionic acid (1.01 g, 35%) as a cream solid: mp 91-93 C.; EI-HRMS m/e calcd for C15H20O2S (M+) 264.1184, found 264.1177.

The synthetic route of 7226-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 16019-33-3, 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde. A new synthetic method of this compound is introduced below.

A mixture of (4,6-dichloro-pyrimidin-5-yl)-acetadehyde (555 mg, 2.91 mmol), N-(trans-4- aminocyclohexyl)-carbamic acid 1 ,1-dimethylethyl ester (623 mg, 2.91 mmol) and DIEA (508 mu, 2.91 mmol) in EtOH (5 mL) was stirred for 18 h at reflux, allowed to cool at rt, concentrated and diluted with DCM/H20. The aqueous layer was extracted with DCM. The combined organic extracts were dried (Na2S0 ), filtered and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, 70:30) to afford to afford 348 mg of the title compound as a white soild: ES-MS: 351.1 [M+H]+; tR= 4.86 min (Method C), Rf = 0.29 (hexane/ethyl acetate, 70:30).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia