Pyrimidines

Synthetic Route of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

Step l:Synthesis of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidineTo a mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 16.28 mmol) in dry DCM (100 mL) was added NCS (4.35 g, 32.6 mmol) at 25 C. The resulting mixture was stirred for 16 hours at 40 C under argon atmosphere. When the 4-chloro-7H-pyrrolo[2,3-d]pyrimidine was consumed, the mixture was filtered directly without cooling. The solid was collected, washed with DCM (20 ml), dried under vacuum to give 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine as a solid. LC-MS: (ES, /// r): 188.01 [M+H]+. H- MR: (300MHz, d6-OMSO, ppm): delta 12.90 (br, 1H), 8.65 (s, 1H), 7.93 (d, J= 2.7Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 3680-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GIRIJAVALLABHAN, Vinay M.; OLSEN, David B.; ZHANG, Zhibo; FU, Jianmin; TANG, Bing-Yu; WO2015/143712; (2015); A1;,
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Electric Literature of 591-55-9, Adding some certain compound to certain chemical reactions, such as: 591-55-9, name is 5-Aminopyrimidine,molecular formula is C4H5N3, 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 591-55-9.

Step 8: 6-Chloro-3-(4-ethylphenylamino)-N-(pyrimidin-5-yl)benzo[d]isoxazole-7-carboxamide 6-Chloro-3-(4-ethylphenylamino)benzo[d]isoxazole-7-carboxylic acid (0.195 g, 0.615 mmol) was dissolved in DMF, followed by TEA (0.223 ml, 1.61 mmol) and HATU (0.285 g, 0.749 mmol). The mixture was allowed to stir for 5 min before adding pyrimidin-5-amine (0.0509 g, 0.535 mmol) and the mixture was heated to 50 C. overnight. The mixture was then cooled to RT, partitioned between EtOAc/brine, the layers were separated, and the aqueous was extracted with EtOAc (3*). The combined organics were washed with H2O and brine, filtered and concentrated. The crude material was purified by silica gel chromatography using 20:1 DCM/MeOH to give 6-Chloro-3-(4-ethylphenylamino)-N-(pyrimidin-5-yl)benzo[d]isoxazole-7-carboxamide as a light brown solid. MS calculated 393.8, found M+H+=394.1.

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. 591-55-9, 5-Aminopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; US2008/227779; (2008); A1;,
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Related Products of 84955-31-7 ,Some common heterocyclic compound, 84955-31-7, molecular formula is C6H5ClN4, 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 2 4-Chloro-5-iodo-2-pivaloylamino-pyrrolo[2,3-d]pyrimidine (I) STR3 A solution of 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (20 g, 118 mmol) and pivaloyl chloride (14.3 g, 118 mmol) in pyridine (150 mL) was stirred for 18 hours at ambient temperature. The resulting dark red solution was evaporated to an amber solid which was co-evaporated with water (20 mL, 3*). The resulting solid was filtered, washed with cold water and then dried over KOH in vacuo to yield 22 g (83%) of 2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine as a reddish solid. 1 H-NMR (DMSO-d6): delta 12.35 (bs, 1, N (7)-H); 10.07 (s,1, N (2)-H); 7.56 (m,1, H-6); 6.58 (m,1, H-5); 1.24 (s, 9, pivaloyl methyls).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84955-31-7, its application will become more common.

Reference:
Patent; Isis Pharmaceuticals, Inc.; US6093807; (2000); A;,
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Pyrimidine – Wikipedia

Reference of 118-70-7, 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. 118-70-7, name is Pyrimidine-4,5,6-triamine, molecular formula is C4H7N5, 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 1 Preparation of 7-Amino[1,2,5]thiadiazolo[3,4-d]pyrimidine A flask was charged with 19.78 g. (0.15 mole) of 4,5,6-triaminopyrimidine and 163.0 g. (137 mole) of thionyl chloride and the mixture stirred at reflux for 18 hours. The dark orange reaction mixture was evaporated to dryness on the rotary evaporator and to the residue was added 500 ml. water and 40 ml. methanol. The resulting solution was adjusted to a pH of 7.5-8.0 with saturated sodium bicarbonate solution and heated to reflux. The hot mixture was filtered and the filtrate cooled to 0-5 C. in an ice-bath. The solid was collected by filtration, washed twice with 50 ml. ice water and twice with 50 ml. ether. The resulting tan product was dried in vacuo at 70 C. overnight to afford 18.2 g. (79%) of product. M.p. 247-249 C.; tlc on silica gel in chloroform-methanol (8:1) showed one spot at Rf =

According to the analysis of related databases, 118-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4098787; (1978); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-59-9, 6-Chloropyrimidin-4-amine, 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, 5305-59-9, blongs to pyrimidines compound. name: 6-Chloropyrimidin-4-amine

The 0.96 g (10 mmol) of 1H-imidazole-4-carbaldehyde was dissolved in 20 ml of DMF, and 1.30 g (10 mmol) of 4-amino-6-chloropyrimidine, 2.07 g (15 mm1) of potassium carbonate was added successively 100 C, stirring reaction 12h. The appropriate amount of water was added and extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and then filtered to remove the solvent under reduced pressure. The residue was purified by silica gel column The eluent was methanol: dichloromethane = 1: 30 to give 0.87 g of a white solid (compound represented by the formula Pialpha) in a yield of 46%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5305-59-9, its application will become more common.

Reference:
Patent; East China University of Science and Technology; Mao Fei; Xu Yixiang; Li Xiaokang; Liu Wenwen; Li Jian; (26 pag.)CN106946854; (2017); A;,
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Reference of 105742-66-3, 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 105742-66-3, name is 4,5-Dichloro-2,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 5 was synthesized as described.33 Compounds 6 and 7were synthesized in our previous work.34 Compounds 4 (5 mmol), 7(5 mmol) and anhydrous potassium carbonate (5 mmol, 0.69 g) wereadded to a mixed solvent of dimethyl formamide (20 mL) and water(10 mL), and then refluxed for 2-4 h. The progress was monitored byTLC. After the reaction was complete, the reaction solution was pouredinto saturated saline and extracted with ethyl acetate (3¡Á80 mL). Theextract was dried, filtered, and the solvent was removed under reducedpressure to give a crude product. Recrystallization from the mixedsolvent of petroleum ether and ethyl acetate gave pure target compoundsO1-17 (Scheme 2).

According to the analysis of related databases, 105742-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yan, Zhongzhong; Liu, Aiping; Ou, Yingcan; Li, Jianming; Yi; Zhang, Ning; Liu, Minhua; Huang, Lu; Ren, Jianwei; Liu, Weidong; Hu, Aixi; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3218 – 3228;,
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Pyrimidine – Wikipedia

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. 36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 36315-01-2

1.2. Synthesis of 2-amino-4,6-dimethoxy-5-nitrosopyrimidine 34.8 g (0.297 mol) of isopentyl nitrite was added to a solution of 41.9 g (0.270 mol) 2-amino-4,6-dimethoxypyrimidine in 675 mL dimethylsulfoxide and stirred for 96 hours at room temperature. After the reaction was complete, the deep blue solution was poured into 2.5 L water and stirred for 1 hour at room temperature. The resulting precipitate was filtered off and washed with water. After drying, 2-amino-4,6-dimethoxy-5-nitrosopyrimidine (32.8 g, 66%) was obtained as a light blue solid. Mp.: 215-218 C. (decomposition) 1H NMR (300 MHz, d6-DMSO): delta=3.94 (s, 6H, 4-OMe, 6-OMe), 8.28 (s, 2H, NH2). 13C NMR (125 MHz, d6-DMSO): delta=54.9 (4-OMe, 6-OMe), 141.9 (5-C), 163.3 (6-C, 4-C), 173-0 (2-C)

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, 36315-01-2, 2-Amino-4,6-dimethoxypyrimidine.

Reference:
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Moch, Melanie; (27 pag.)US2016/296447; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4595-59-9, 5-Bromopyrimidine, 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, 4595-59-9, blongs to pyrimidines compound. HPLC of Formula: C4H3BrN2

General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3¡Á15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Article; Liu, Chun; Li, Xinmin; Gao, Zhanming; Wang, Xinnan; Jin, Zilin; Tetrahedron; vol. 71; 23; (2015); p. 3954 – 3959;,
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Application of 24415-66-5 , The common heterocyclic compound, 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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.

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 240 mg (about 1.5 mmol) of 1-ethyl-2-methyl-1H-indole,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 107 mg of pure product e6, which was a purple solid with a yield of 73%;

The synthetic route of 24415-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
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Pyrimidine – Wikipedia

Application of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde, molecular formula is C5H4N2O, 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.

Pyrimidine-5-formaldehyde (1.00 g, 9.25 mmol),2,4-Dimethylphenylhydrazine hydrochloride (1.60 g, 9.30 mmol)And DMF (16 mL) was added to a 100 mL single-neck round bottom flask in turn.Reaction at room temperature for 1 h,Neutralize the hydrochloride with 8 mL of saturated sodium bicarbonate solution, then add water (80 mL).A yellow solid precipitated, and the solid was filtered, washed with water (50 mL¡Á2).Dissolve in dichloromethane (20 mL), separate the layers, and collect the organic phase.The title compound was obtained as a yellow solid (1.20 g, 57.0%).

According to the analysis of related databases, 10070-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Chen Kangzhi; Jin Chuanfei; Luo Ming; Zhang Yingjun; (28 pag.)CN108863948; (2018); A;,
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