Pyrimidines

Reference of 63234-80-0, 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.63234-80-0, name is 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one, molecular formula is C11H15ClN2O, molecular weight is 226.7026, as common compound, the synthetic route is as follows.

General procedure: A creamy white solid of 3-(2-chloroethyl)- 2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a] pyrimidin-4-one (5) (1.0eq) in N,N-dimethylformamide was taken, pottasium carbonate (3.0 eq) was added to the reaction mixture and then the appropriate aliphatic/ aromatic/heterocyclic amines (1.0 eq) were added and the reaction mixture was heated at 80 ¡ãC for 8h. The progress of the reaction was monitored by TLC. Upon completion, the solvent was removed by water wash and extracted with ethyl acetate. The organic layer was washed with 10percent ammonium chloride solution and finally water wash was given to organic layer and dried with anhydrous sodium sulphate. The solvent was evaporated to get crude product which was purified by column chromatography over silica gel (60-120mesh) using hexane: ethyl acetate(8:2) as an eluent.

Statistics shows that 63234-80-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one.

Reference:
Article; Krishnamurthy, Byregowda; Vinaya, Kambappa; Rakshith, Devraj; Prasanna, Doddakunche Shivaramu; Rangappa, Kanchugarakoppal Subbegowda; Medicinal Chemistry; vol. 9; 2; (2013); p. 240 – 248;,
Pyrimidine | C4H4N2 – PubChem,
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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

To a solution of cyclopropylmethanol (1.908 g, 26.5 mmol) in THF (200mL) was addedsodium hydride (3.17 g, 79 mmol) in an ice bath. After stirred for 30 mm, 4,6-dichloro-1H- pyrazolo[3,4-d]pyrimidine (5 g, 26.5 mmol). The reaction mixture was gradually allowed to room temperature and stirred overnight. Then the mixture was diluted with water (80 mL), concentrated to remove solvent and diluted with ethyl acetate (220 mL). The organic layerwas washed with water (80 mLx 2), dried over Na2SO4, filtered and concentrated. The crude(5 g, 84% yield) was directly used into next step.LCMS: 225[M+H]. tR2.9l8 (LCMS condition 1)

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, 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DING, Xiao; LIU, Qian; LONG, Kai; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; XU, Qiongfeng; EDGE, Colin Michael; WO2015/113451; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 74-69-1, 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.74-69-1, name is 2-Methyl-4-pyrimidinamine, molecular formula is C5H7N3, molecular weight is 109.1292, as common compound, the synthetic route is as follows.

Preparation 427: 5-chloro-2-((2-methylpyrimidin-4-yl)amino)pyrimidin-4-ol (2333) CS2CO3 (27.0 g, 83 mmol) was added to a solution of 2,5-dichloropyrimidin-4-ol (6.5 g, 39.4 mmol) and 2-methylpyrimidin-4-amine (4.51 g, 41.4 mmol) in DMF (100 mL, 1291 mmol). The mixture was degassed (3 x with nitrogen) then [Pd(allyl)tBuBrettPhos)]OTf (Pd-175) (0.646 g, 0.827 mmol) was added. The reaction was further degassed then placed under nitrogen and heated to 95C for 3 h, then at room temperature overnight. Et20 (300 mL) was added and the resulting pale yellow solid collected by filtration and washed with Et20 (150 mL). The solid was suspended in DCM (100 mL) and 4M HCI in dioxane (60 mL) was added in portions (pH = 1). The pale yellow solid was collected by filtration and washed with DCM (50 mL) then dried in vacuo to afford the title compound (38.66 g). The product, which contained a mixture of cesium salts, was used wihtout further purification in the next step. LCMS: [M+H]+ = 238.

The chemical industry reduces the impact on the environment during synthesis 74-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Pyrimidine – Wikipedia

Application of 1193-24-4 ,Some common heterocyclic compound, 1193-24-4, molecular formula is C4H4N2O2, 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.

0.5 mol of 4,6-dihydroxypyrimidine was added to the reaction vessel,Solvents Trichloromethane,0.05 mol of pyridine catalyst,Then slowly into the phosgene 1.5mol,The reaction temperature was controlled within 50 C,After reaction for 3 h,After the completion of the reaction, the excess solvent chloroform was distilled off under reduced pressure,To give a 4,6-dichloropyrimidine solution,And then filtered, concentrated and crystallized to give 4,6-dichloropyrimidine as white needles.The yield of product 4,6-dichloropyrimidine prepared by the above method was 78% and the purity was 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; Anhui Guangxin Agrochemical Co., Ltd; Huang, Jinxiang; Guo, Xuejun; Wu, Jianping; Hu, Minghong; Huang, Yaming; Cheng, Weijia; Li, Hongwei; Xu, Xiaobing; Gao, Yanbing; Dai, Yuting; (4 pag.)CN105859637; (2016); A;,
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Pyrimidine – Wikipedia

Reference of 60025-09-4, 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. 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile, molecular formula is C5H3ClN4, 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.

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

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 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14080-23-0, Adding some certain compound to certain chemical reactions, such as: 14080-23-0, name is 2-Cyanopyrimidine,molecular formula is C5H3N3, 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 14080-23-0.

To a stirring solution of 2-cyanopyrimidine (2.0 g, 19.0 mmol) in methanol (50 mL) were added 10%Pd/C (300 mg), 12 N HCI (1.5 mL) under 2 atmosphere. The reaction mixture was stirred under atmosphere (balloon pressure) at RT for 3 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with methanol. Obtained filtrate was concentrated under reduced pressure to afford crude compound which was triturated with diethyl ether to obtained compound 2S-Y (1.2 g, 44%) as white solid. 1H-NMR: (500 MHz, DMSO-i): delta 8.87 (d, J= 5.0 Hz, 2H), 8.69 (br s, 2H), 7.52 (t, J= 5.0 Hz, 1H), 4.24 (s, 2H); Mass (ESI): 1 10.3 [M++l]

According to the analysis of related databases, 14080-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAUREX, INC.; LOWE, John, A., III; KHAN, M., Amin; WO2014/120783; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, 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, Computed Properties of C15H13ClN2O4, blongs to pyrimidines compound. Computed Properties of C15H13ClN2O4

Methyl (¡ê)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (¡ê)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2; Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (¡ê)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 37554-70-4 ,Some common heterocyclic compound, 37554-70-4, molecular formula is C5H4ClFN2O, 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.

General procedure: (5-Fluoro-4-methoxypyrimidin-2-yl)isobutylamine; To a stirred solution of 2-chloro-5-fluoro-4-methoxypyrimidine (10.0 g, 61.7 mmol) and isobutylamine (6.8 g, 92.6 mmol) in MeCN (200 ml) was added DIEA (11.9 g, 92.6 mmol). The mixture was stirred at 80 C for 12 h. At the end of the reaction, the resulting mixture was cooled and partitioned between EtOAc (200 ml) and H2O (200 ml). The EtOAc layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2-5% EtOAc/PE to afford 5.2 g (42% yield) of the product as a yellow solid.1H NMR (400 MHz, CDCl3) delta 7.92 (d, J = 2.8 Hz, 1H), 5.03 (br s, 1H), 3.99 (s, 3H), 3.21 (t, J = 6.4 Hz, 2H), 1.91 (m, 1H), 0.99 (d, J = 6.4 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37554-70-4, its application will become more common.

Reference:
Article; Wada, Hiroki; Cheng, Lili; Jiang, Ji; Jiang, Zhigan; Xie, Jun; Hu, Tao; Sanganee, Hitesh; Luker, Tim; Tetrahedron Letters; vol. 53; 14; (2012); p. 1720 – 1724;,
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Pyrimidine – Wikipedia

Reference of 4318-56-3, 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 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 6-Chloro-3-methylpyrimidine-2,4 (l/7,3/7)-dione (43 g, 267 mmol), (1192) K2C03 (92.1 g, 667 mmol) and PMB-C1 (1.4 g, 28.0 mmol) were taken up in DMF (500 mL). The reaction mixture was stirred at 50 C for 16 hours. The mixture was partitioned between H20 (1000 mL) and EtOAc (1500 mL) and the aqueous phase was extracted with EtOAc (800 mL x 2). The combined organics were washed with brine (500 mL x 2), dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give a residue.Trituration with petroleum ether/EtOAc (10 : 1) resulted in the formation of a precipitate which was collected by filtration, washed with petroleum ether/EtOAc (10 : l, 100 mL), and dried to give 6-chloro-l-(4-methoxybenzyl)-3-methylpyrimidine-2, 4(1/7, 3/7)-dione (50.0 g, 66.7% yield) as a white solid.

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 4318-56-3, 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; WALTERS, W., Patrick; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; TAYLOR, Alexander, M.; PIERCE, Levi Charles, Thomas; MURCKO, Mark, Andrew; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; BHAT, Sathesh; KONZE, Kyle; DAHLGREN, Markus, Kristofer; THERRIEN, Eric; (0 pag.)WO2019/165073; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62458-96-2, 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. 62458-96-2, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one, molecular formula is C14H15N3O, 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 39 7- (3-Chloropyridin-2-yl)-5, 6,7, 8-tetrahydro-N-phenethylpyrido [3,4-d] pyrimidin-4-amine A. 5,6, 7, 8-Tetrahydropyrido [3,4-d] pyrimidin-4 (3H) -one [00306] 7-Benzyl-5, 6,7, 8-tetrahydropyrido [3,4-d] pyrimidin-4 (3H)-one (1. 5g, 6.2mmol) was dissolved in methanol (25mL) and palladium hydroxide was added (1. 5g, 20% wt). The mixture was shaken on a Parr Shaker under H2 (g) atmosphere (60 PSI) for 3 days. The mixture was filtered through celite and evaporated to give 0.9g of material as a yellow solid (96%), which was used as such for the next step.

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 62458-96-2, 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one.

Reference:
Patent; RENOVIS, INC.; WO2005/66171; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia