Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, 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, Formula: C4HCl2FN2, blongs to pyrimidines compound. Formula: C4HCl2FN2

Stage 3 (0508) 4,6-Dichloro-5-fluoro-pyrimidine (1 eq), 3,4-dichlorophenyl boronic acid (0.7 eq) and Pd(PPh3)4 (0.05 eq) were suspended in 1,4-dioxane (20 vol). A 2M K2CO3 solution (6.75 vol) was added and the reaction mixture was heated at 90 C. with stirring for 2 hours under an atmosphere of N2. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in EtOAc and water. The mixture was partitioned and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography (eluent: [1:15] EtOAc:heptane) to afford the required target compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; Wityak, John; Toledo-Sherman, Leticia M.; Dominguez, Celia; Courtney, Stephen Martin; Yarnold, Christopher John; De Aguiar Pena, Paula C.; Scheel, Andreas; Winkler, Dirk; US9145373; (2015); B2;,
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Pyrimidine – Wikipedia

Related Products of 53554-29-3, 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. 53554-29-3, name is Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate, molecular formula is C8H10N2O3S, 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.

In a 500 mL autoclave, Compound 1 (214 g, 1 mol) and 200 mL of 30% by mass of hydrogen peroxide were added.Gradually heat up to 120 C to carry out the reaction, after the reaction is over,The autoclave was cooled to room temperature, and the reaction solution was spun dry.Recrystallization from ethanol gave a white solid in a yield of 95%.

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 53554-29-3, Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate.

Reference:
Patent; Chongqing Aoshe Biochemical Co., Ltd.; Cui Zhenwei; Zhang Weiwei; Zhang Fuqing; (8 pag.)CN109232542; (2019); A;,
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Pyrimidine – Wikipedia

Electric Literature of 74840-47-4, 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 74840-47-4, name is 5-Chloro-2-methylpyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

A 4 mL Wheaton scintillation vial was charged with 280 pL of a 0.6 mlvi solution of 5- chloro-2-methylpyrimidine-4-carboxylic acid in N,N-dimethylacetamide (30.0 mg, 1.2 equivalents, 0.2 mmol), a 500 pL solution of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5- b]pyridinium 3-oxid hexafluorophosphate in N,N-dimethylacetamide (58.5 mg, 1.1 equivalents, 0.15 mmol, HATU), a 500 pL solution of methyl 5-[(3-phenylpropyl)amino]pentanoate hydrochloride in N,N-dimethylacetamide (40.0 mg, 0.14 mmol, Example 149-Step 2), neat triethylamine (58.9 pL, 3 equivalents, 0.42 mmol), and a stir bar. This was capped with a white seal and microwave cap for an Anton Paar microwave reactor. The vial was heated in an Anton Paar Synthos 3000 parallel microwave optimizer for 15 minutes at 120 C. Upon completion, the reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was then dissolved in 1000 pL of dioxane. To this, 1000 pL of a 1 M LiOH aqueous solution in 75% CH3OH was added. The mixture was then heated at 60 C for 1 hour. The reaction mixture was then filtered once more and concentrated under reduced pressure. The residue was re-dissolved in dimethyl sulfoxide/methanol and purified using preparative-HPLC to give the titled compound (42.3 mg, 73.6%). ?H NMR (400 MHz, DMSO-d6) ppm 8.72 (d, J = 35.5 Hz, 1H), 7.31 -7.08 (m, 4H), 6.97(a, J = 7.4 Hz, 1H), 3.52 – 3.41 (m, 2H), 3.09 – 3.05 (m, 1H), 2.66 (t, J = 7.6 Hz, 1H), 2.59 (a, J =23.0 Hz, 3H), 2.43 (t, J = 7.3 Hz, 1H), 2.26 (t, J = 6.9 Hz, 1H), 2.06 (t, J = 7.2 Hz, 1H), 1.94 (p, J =7.5, 6.9 Hz, 1H), 1.80 (dt, J = 13.0, 6.2 Hz, 2H), 1.70- 1.56 (m, 3H), 1.50 (q, J = 8.2, 7.8 Hz, 1H),1.35 (p, J = 6.8 Hz, 1H); MS (APCf) m/z 390.0 (M+H).

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 74840-47-4, 5-Chloro-2-methylpyrimidine-4-carboxylic acid.

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 874-14-6, 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. 874-14-6, name is 1,3-Dimethyluracil, molecular formula is C6H8N2O2, 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.

A mixture of A-5 (8.00 g, 96.28 mmol), 1,3-dimethylpyrimidine-2,4-dione (13.49 g, 96.28 mmol) and EtONa (32.76 g, 481.40 mmol) in EtOH (150 mL) was stirred at 80 °C for 5 hours. The solid was collected by filtration, washed with EtOH (50 mL), and dried in an oven to afford A-6 (12.50 g, 92.51 mmol) as a solid. 1H NMR (400MHz, DMSO-d6) delta 11 7.97 (d, 1H), 7.43 (d, 1H), 5.62 (d, 1H), 5.35 (d, 1H).

According to the analysis of related databases, 874-14-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14001-67-3, 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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine. A new synthetic method of this compound is introduced below.

Step 1 After purged with nitrogen, mixture of 5-bromo-2-(methylthio)pyrimidine (1.0 g, 4.9 mmol), tris(dibenzylideneacetone)dipaliadium(0) (0.45 g, 0.49 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.56 mg, 0.98 mmol), cesium carbonate (2.38 g, 7.3 mmol) and dioxane (20 mL) was added to 4-(5-fluoro-2-pyridyloxy)aniline (1.0 g, 4.9 mmol), and stirred under heating at reflux for 24 hours. The reaction mixture was added to saturated chloride ammonium aqueous solution, and extracted with ethyl acetate. The organic phase was washed by saturated saline, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The resulting residue was purified by silica-gel column chromatography (ethyl acetate/hexane). The resulting mixture was solidified by diisopropyl ether to give 5-[4-(5-fluoro-2-pyridyloxy)phenylamino]-2-(methylthio)pyrimidine (0.51 g, yield: 32%) as pale yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 2.57 (3H, s), 5.48 (1H, s), 6.89-6.95 (1H, m), 7.03-7.11 (4H, m), 7.45 (1H, m), 8.02 (1H, s), 8.40 (2H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14001-67-3, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; TANAKA, Satoru; HIRAMATSU, Yoshiharu; NOZU, Azusa; NAKAMURA, Ken’ichioh; (260 pag.)US2016/24072; (2016); A1;,
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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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Reference Example 60 (R)-1-(2-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N-methylpiperidine-3-carboxamide Diisopropylethylamine (3.7 ml, 21.2 mmol) was added into chloroform (25 ml) solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1 g, 5.29 mmol) prepared in Step 3 of Reference Example 52 and (R)-(-)-3-piperidincarboxylic acid (0.75 g, 5.82 mmol), and they were stirred at 70 C. overnight. After cooing the reaction solution to room temperature, methylamine hydrochloride (0.36 g, 5.29 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (1.1 g, 5.82 mmol) and 1-hydroxybenzotriazole hydrate (0.79 g, 5.82 mmol) were added thereto, and they were stirred at room temperature overnight. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized by using ethyl acetate to give the titled compound (1.1 g) as a white solid. 1H NMR (400 MHz, CDCl3) delta 6.31 (brs, 1H), 4.21 (d, 1H), 4.07 (d, 1H), 3.60 (t, 1H), 3.30 (t, 1H), 2.97 (t, 2H), 2.95-2.75 (m, 5H), 2.42 (brs, 1H), 2.15-2.00 (m, 3H), 2.00-1.90 (m, 1H), 1.80-1.70 (m, 1H), 1.55 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 5466-43-3.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Intermediate 216 2-(4-methylchroman-5-yl)oxy-5-nitro-pyrimidine [1137] [1138] 4-methyl-3,4-dihydro-2Hchromen-5-ol (Intermediate 211, 111 mg, 0.676 mmol) was dissolved in 5.0 mL of DMF. K2CO3 (140 mg, 1.01 mmol) and 2-chloro-5-nitropyrimidine (162 mg, 1.01 mmol) were added and the reaction mixture was stirred for 1 hour at room temperature. DMF was then evaporated under high vacuum and the residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate from 1:0 to 7:3 as eluents affording the title compound (192 mg). [1139] 1H NMR (400 MHz, CDCl3) delta ppm 9.36 (2H, s), 7.21 (1H, t), 6.85 (1H, d), 6.68 (1H, d), 4.15-4.35 (2H, m), 2.90-3.02 (1H, m), 2.08-2.20 (1H, m), 1.65-1.75 (1H, m), 1.29 (3H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10320-42-0, its application will become more common.

Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; Alvaro, Giuseppe; Dambruoso, Paolo; Tommasi, Simona; Decor, Anne; Large, Charles; US2013/267510; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4316-93-2, 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. 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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.

Step 1: A solution of dibenzylamine (10.2 g) in dichloromethane (30 mL) is dripped into a solution of 4,6-dichloro-5-nitropyrimidine (10 g) in dichloromethane (70 mL) on an ice bath. Then triethylamine (14.4 mL) is added, and the mixture is stirred for 1 hour. Water is added to the reaction mixture, the organic layer is washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent is concentrated under reduced pressure to obtain N,N-dibenzyl-6-chloro-5 -nitropyrimidine-4-amine (19.2 g).

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 4316-93-2, 4,6-Dichloro-5-nitropyrimidine.

Reference:
Patent; ACERTA PHARMA B.V.; IZUMI, Raquel; SALVA, Francisco; HAMDY, Ahmed; WO2015/181633; (2015); A2;,
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. 1193-24-4, name is 4,6-Dihydroxypyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C4H4N2O2

(Ref: A. Gomtsyan, S. Didomenico, C-H. Lee, M. A. Matulenko, K. Kim, E. A. Kowaluk, C. T. Wismer, J. Mikusa, H. Yu, K. Kohlhass, M. F. Jarvis, S. S. Bhagwat; J. Med. Chem., 2002, 45, 3639-3648.) A mixture of DMF (32 mL) and POCl3 (100 mL) at 0 C. was stirred for 1 hour, treated with 4,6-dihydroxypyrimidine (25.0 g, 223 mmol), and stirred for 0.5 hour at room temperature. The heterogeneous mixture was then heated to refluxed and stirred for 3 hours. The reaction was cooled to room temperature and the resulting viscous, black liquid was poured onto ice water and extracted with diethyl ether (6×100 mL). The organic phase was subsequently washed with NaHCO3, and water, dried over MgSO4, and concentrated to give 25 as a yellow solid (20.0 g, 57% yield). 1H NMR (CDCl3) delta 10.41 (s, 1H), 8.85 (s, 1H).

The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2007/72864; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1780-31-0, 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 1780-31-0, name is 2,4-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloro-5-methylpyrimidine (50 g, 0.31 mol), water (500 mL) and zinc dust (50 g, 0.94 mol) was heated at reflux overnight. The reaction mixture was filtered and the filtrate was extracted with dichloromethane (3*500 mL). The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from petroleum ether to afford compound C60 as a white solid. Yield: 27.9 g, 0.22 mol, 75%. LCMS m/z 129.3 (M+1). 1H NMR (400 MHz, CDCl3) delta 2.25 (s, 3H), 8.40 (5, 2H).

According to the analysis of related databases, 1780-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US2010/190771; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia