Pyrimidines

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. 20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Diaminopyrimidine-5-carboxaldehyde

EXAMPLE 10 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde, and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture was heated at reflux for 4 hours, allowed to cool to room temperature, and the precipitated product was filtered and washed with diethyl ether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]-pyrimidine, mp 325-332 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, 20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde.

Reference:
Patent; Warner-Lambert Company; US5620981; (1997); A;,
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Related Products of 28969-60-0 ,Some common heterocyclic compound, 28969-60-0, molecular formula is C4H2Cl3N3, 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 A5 To a flask under argon was added 4-amino-2,5,6-trichloropyrimidine (0.08564 mol), 4-amino-benzonitrile (0.1071 mol), 1-methyl-2-pyrrolidinone (17 ml) and HCl in diethylether (1M; 85.6 ml). The mixture was placed in an oil bath at 130 C. under a stream of nitrogen until the ether was gone. An additional 10 ml of 1-methyl-2-pyrrolidinone was added. The mixture was heated at 145 C. for 16 hours under argon. 1,4-Dioxane was added. The mixture was refluxed, cooled, then filtered. The filtrate was evaporated. The residue was dissolved in CH2C1-2, washed with 1 N NaOH, then filtered. The solid was dissolved in 2-propanone, evaporated onto silica gel, and chromatographed using 1-3% 2-propanone in hexane as eluent. The pure fractions were collected and the solvent was evaporated, yielding 1.63 g (6.8%) of 4-[(4-amino-5,6-dichloro-2-pyrimidinyl)amino]benzonitrile (interm. 12).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,28969-60-0, its application will become more common.

Reference:
Patent; Kukla, Michael Joseph; Ludovici, Donald William; Kavash, Robert William; De Corte, Bart Lieven Daniel; Heeres, Jan; Janssen, Paul Adriaan Jan; Koymans, Lucien Maria Henricus; de Jonge, Marc Rene; Van Aken, Koen Jeanne Alfons; Krief, Alain; US2003/186990; (2003); A1;,
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Synthetic Route of 1780-26-3 ,Some common heterocyclic compound, 1780-26-3, molecular formula is C5H4Cl2N2, 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.

Into aclean and dry 5 L 4 N round bottom flask connected to a mechanical stirrer and equipped with a condenser and thermometer socket is charged under stirring, 200 g of 2-amino-thiazole-N-(2-chloro-6-methylphenyl)-5-carboxamide, 146 g of 4,6-dichloro-2-methylpyrimidine and 2 L of THF under a nitrogen atmosphere. After clear solution, cooled the mass temperature to 10-20 C. Added 30 % sodium-t-butoxide solution to the reaction mass over a period of 60-75 min at 10-20 C and brown coloured solution formation is observed. Raised the reaction mass temperature to 25-30 C and maintained the mass temperature to 25-30 C for 90-120 min. After HPLC compliance cooled the mass temperature to 0-5 C and added 2 N HCl solution to the reaction mass over a period of 60-90 min at 0-5 C. Maintained the mass temperature at 0-5 C for 105-120 min and transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. Washed the wet cake with 600.0 mL of water and dried the wet material in a drier at 60-65 C for 8-10 h gave 210.0 g of the title compound with purity above 99 %. Off white colour solid; Elemental analysis C16H13N5OSCl2calcd (found) %: C 48.74 (48.91), H 3.32 (3.45), N 17.76 (15.97),O 4.06 (4.24), S 8.13 (8.29). IR (KBr, numax, cm-1): 3424.28,3241.22, 2876.23-2789.82, 1638.82, 770.36; 1H NMR (400MHz, DMSO-d6): delta2.247 (s, 3H, -CH3), 2.594 (s, 3H, -CH3),6.952 (s, 1H, ArH), 7.252-7.314 (m, 2H, ArH), 7.403-7.422(dd, 1H, ArH), 8.320 (s, 1H, ArH), 10.030 (s, 1H, -NH), 12.251(s, 1H, -NH); 13C NMR (100 MHz, DMSO-d6): delta167.38, 161.23,159.52, 158.48, 157.51, 140.76, 138.74, 133.28, 132.35, 129.02,128.24, 127.18-126.99, 103.40, 66.97, 25.12, 18.23; ESI-MS(m/z): 394.14 (M+1), 396.15 (M+3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1780-26-3, its application will become more common.

Reference:
Article; Buchappa; Sagar Vijay Kumar; Durga Prasad; Aparna; Asian Journal of Chemistry; vol. 30; 7; (2018); p. 1621 – 1628;,
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Application of 10457-14-4, 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. 10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine. A new synthetic method of this compound is introduced below.

To a stirred solution of 16 (3.4326 g, 8.2913 mmol, 1 eq.) in CH2Cl2 (100 mL) at 0 C, was added2,4-O,O-bis(trimethylsilyl)uracil (6.3677 g, 24.8739 mmol, 3 eq.) and trimethylsilytrifluoromethanesulfone(3.0 mL, 16.5826 mmol, 2 eq.) and stirring was continued at 0 C for 2h and atroom temp for 3 h. The reaction was quenched with saturated aq. NaHCO3 at 0 C. The organiclayer was separated and the aqueous layer was extracted with ethyl acetate. The organic layerswere combined and dried over MgSO4. Solvent was removed under reduced pressure and theresidue was purified by silica gel chromatography (hexanes-ethyl acetate, 1:1) to afford 17(3.1305 g, 94%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10457-14-4, 2,4-Bis((trimethylsilyl)oxy)pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Kiran; Wakamatsu, Hideaki; Natori, Yoshihiro; Takahata, Hiroki; Yoshimura, Yuichi; Tetrahedron Letters; vol. 54; 30; (2013); p. 3949 – 3952;,
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Reference of 7627-44-3, 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. 7627-44-3, name is 2,4-Dichloro-5-(iodomethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Step 5: Intermediate 5 [00557j To a 125 mL tube was added Intermediate 4 (360 mg, 1.60 mmol) 2,4-dichloro-5- (iodomethyl)pyrimidine (461 mg, 1.60 mmol) and DIPEA (848 tl, 4.79 mmol) in DMA (4 mL). The tube was sealed and the reaction mixture heated to 65 °C with stirring for 4 h after which it was cooled, concentrated and co-evaporated with toluene several times. The resultant oil was dissolved in EtOAc, and solids were removed by filtration. The filtrate was concentrated, dissolved in DCM and purified through flash chromatography on silica gel (eluting with EtOAc/hexanes) to provide 350 mg of the title compound. MS mlz: 350.3 (M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7627-44-3, 2,4-Dichloro-5-(iodomethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); A1;,
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Synthetic Route of 588-36-3, Adding some certain compound to certain chemical reactions, such as: 588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine,molecular formula is C6H9N3OS, 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 588-36-3.

To a stirred solution of (4-amino-2-(methylthio)pyrimidin-5-yl)methanol (3.05 g, 17.81 mmol) in dichloromethane (150 mL) was added manganese dioxide (12.5 g, 144 mmol) and the mixture was stirred overnight. The mixture was filtered through a pad of Celite and the filter cake was washed with dichloromethane (150 mL, 2X) and the filtrate was concentrated to give 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (1 .76 g, 10.40 mmol, 58 % yield) as a white solid. The Celite filter cake was further washed with methanol (150 mL). This filtrate was evaporated to dryness to give 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (486 mg, 2.87 mmol, 16 % yield) as a light gray solid. 1H NMR (400 MHz, CD3SOCD3) delta 3.34 (s, 3 H), 8.03 (br s, 1 H), 8.31 (br s, 1 H), 8.58 (s, 1 H), 9.77 (s, 1 H); LC-MS (LC-ES) M+H = 170.

According to the analysis of related databases, 588-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; SHEARER, Barry George; YOUNGMAN, Mark Andrew; (214 pag.)WO2018/229629; (2018); 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 116436-03-4, name is 2,4-Diamino-6-ethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 116436-03-4

General procedure: A solution of 6-morpholinopyrimidine-2,4-diamine 1a (5.0 g, 25.6 mmol) and potassium thiocyanate (14.9 g, 0.15 mol) in DMF (120 ml) was heated at 65 C. Pyridine (4.14 ml, 51.2 mmol) was added and the solution cooled to 5 C. Bromine (1.31 ml, 25.6 mmol) was added slowly and the reaction mixture stirred for 2 h at 5-10 C. The reaction mixture was poured into ice-water (100 ml) and stirred for 1 h. The volatiles were removed under reduced pressure and the resulting solid was diluted with water, filtered and dried. The crude solid was purified by flash chromatography on silica gel (CH2Cl2/MeOH 30:1) to yield the title compound as white solid (3.61 g, 56%).

With the rapid development of chemical substances, we look forward to future research findings about 116436-03-4.

Reference:
Article; Jang, Mi-Yeon; Jonghe, Steven De; Segers, Kenneth; Anne, Jozef; Herdewijn, Piet; Bioorganic and Medicinal Chemistry; vol. 19; 1; (2011); p. 702 – 714;,
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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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, 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. COA of Formula: C13H10ClN3

To a 250 mL three-necked flask was added 3- (2-chloropyrimidin-4-yl) -1-methylindole (2.430 g, 10 mmol)4-fluoro-2-methoxy-5-nitroaniline (2.418 g, 13 mmol)And p-toluenesulfonic acid monohydrate (2.850 g, 15 mmol)And 80 mL of 2-pentanol was added,Start stirring and heating,80 reflux 2.5h,After completion (CHCl3:MeOH = 8:1, Rf = 0.5 ) detection reaction, TLC Turn off heating,From a bottle of three bottles with a needle through the plastic plug and slowly into the amount of ethanol,As the temperature decreases,Precipitation of yellow solid,Ice bath to continue to precipitate solid,Filtration, ethanol washing,Dried to give 3.431 g of compound 3 as a yellow solid,Yield 87%.

With the rapid development of chemical substances, we look forward to future research findings about 1032452-86-0.

Reference:
Patent; Beijing University of Technology; Yan Hong; Zhao Zhichang; Hu Shengquan; Feng Wenyan; Li Peng; Song Xiuqing; (9 pag.)CN106967050; (2017); A;,
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Reference of 50270-27-4, 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. 50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde, molecular formula is C5HCl3N2O, 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 Compound 7A (2.1 14 g, 10 mmol) and sulfanilamide (1.722 g, 10 mmol) in dioxane (80 mL) was stirred in an oil bath at 40-50 0C for 10 minutes, and then at room temperature overnight. The mixture was evaporated in vacuo to give a solid, which was washed with methylene chloride and water; and then dried to give Compound 7B as yellow solid (3.Og, 78percent based on HCI salt). 1H NMR ((CD3)2SO) delta 1 1.1 (s, IH), 10.3 (s, IH), 9.85 (d, 2H), 9.80 (d, 2H), 7.35 (s, 2H); MS 346 (M-I-H+).A mixture of Compound 7B (173.6 mg, 0.5 mmol) and benzyl amine (109.2 uL, 1.0 mmol) in THF (5 mL) was stirred at room temperature overnight. The mixture was evaporated in vacuo and then was subjected to HPLC separation to give Compound 7C as HCl salt (13.1 mg, 5percent based on HCl salt). MS 418 (M+H+), 440 (M+Na+).7C *A mixture of Compound 7C (IO mg, 0.024 mmol) and hydrazine (20 uL) in methanol (1 mL) was refluxed for 30 minutes; and then evaporated to dryness. The residue was washed with water and dried to give Compound 2 as a pale yellow solid (4 mg, 42percent). 1H NMR ((CD3)2SO) delta 8.2 (s, IH), 7.8 (m, 4H), 7.6-7.3 (m, 8H), 4.7 (s, 2H); MS 396 (MH-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 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/39359; (2008); A2;,
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Pyrimidine – Wikipedia

Reference of 1197953-49-3, 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. 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. A new synthetic method of this compound is introduced below.

Compound a6 (150 mg, 0.5 mmol) was dissolved in acetone/water (3:1 by volume,A total of 8 mL), adding compound b3-1 (200 mg, 0.6 mmol), 3 drops of concentrated hydrochloric acid, sealed, heated to 100 C, stirred overnight.Cool to room temperature and adjust to pH 12 with 10% aqueous sodium hydroxide.Extract three times with dichloromethane, dry the organic phase, filter and concentrate.Column chromatography was carried out with ethyl acetate, dichloromethane/methanol (10:1 by volume) as mobile phase.Yield 110 mg of a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1197953-49-3, its application will become more common.

Reference:
Patent; Zhejiang Tongyuankang Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Wang Xin; Wu Shiyong; Li Jingya; Guo Ruiyun; Zheng Maolin; Liang Apeng; Wang Guohui; Chen Mingtao; Ma Jie; Niu Chengshan; (65 pag.)CN108689994; (2018); A;,
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