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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 1337532-51-0

To a stirred solution of mixture of 1-(4-bromo-3-fluorophenyl)-3-(m-tolyl)pyrrolidin-2-one (0.5 g, 1.4 mmol, 1.0 equiv), was added bis(pinacolato)diboron (0.365 g, 1.4 mmol, 1.0 equiv), and potassium acetate (0.422 g, 4.3 mmol, 1.0 equiv), and the mixture was degassed with Argon for 10 minutes then PdCl2(dppf)-CH2Cl2 adduct (0.05 g, 0.072 mmol, 0.05 equiv) was added and again degassed with Argon for 10 minutes. The reaction mixture was stirred for 3 hours at 100 C in a sealed vessel. The reaction was cooled to room temperature. 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.326 g, 1.436 mmol, 1.0 equiv) and saturated aqueous NaHC03 (6 mL) was added, and Argon gas was bubbled through the reaction mixture for 10 minutes and PdCl2(dppf)-CH2Cl2 adduct (0.05 g, 0.072 mmol, 0.05 equiv) was added. The vessel was sealed, and the reaction mixture was stirred overnight at 100 C. The crude mixture was filtered through celite and the filtrate was extracted with EtOAc and dried over Na2S04 and concentrated. Purification: Purified by flash column chromatography using silica gel column, using 3 to 4 % MeOH in DCM as eluent to get desired product as white color solid. Yield: (0.055 g, 9.23%); LCMS (ES) m/z = 416.2 [M+H]+. H NMR (400 MHz, DMSOd6) delta 2.16 – 2.23 (m, 1 H), 2.30 (s, 3 H), 2.57 – 2.65 (m, 1 H), 3.74 (s, 3 H), 3.91 – 4.01 (m, 3 H), 5.98 (br s, 2 H), 7.10 (t, J=6.8 Hz, 3 H), 7.23 (t, J=6.80 Hz, 1 H), 7.30 (s, 1 H), 7.42 (t, J=8.4 Hz, 1 H), 7.59 (d, J=7.60 Hz, 1 H), 7.83 (d, J=12.8 Hz, 1 H), 8.14 (s, 1 H).

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, 1337532-51-0, 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
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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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, 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. Formula: C16H30N2Sn

A mixture containing 4tau(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90 0C overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 153435-63-3.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
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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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

EXAMPLE 1; Preparation of the Compound of Formula (II); In a 50 mL round bottomed flask equipped with a magnetic stirrer, condenser, Ar inlet, temperature controller (J-Kem) and heating mantle was introduced compound (1) (1.0 g, 2.53 mmoles, HPLC 95.28%), N-methylpyrrolidone (6.5 mL), piperazine (0.26 g, 3.043 mmoles, 1.2 eqs) and diisopropylethylamine (0.88 mL, 5.072 mmoles, 2 eqs). The suspension was heated at 120 C. for 45 min (HPLC showed 56.3% (II), 21.1% (2) and 0.6% of starting (1)). The mixture was cooled at r.t. and diluted slowly with water (27.8 mL) to precipitate the product. The solid was collected by filtration and rinsed with water (14 mL). The solid collected showed only 45.2% of (II) along with 31.4% (2)). A white solid also crystallized out of the filtrate. The material was collected by filtration and dried under high vacuum at 40 C. for 16 hrs to give 0.22 g (0.49 mmole, 19.6% yield) of (II) as a white solid (HPLC 86.9%). HPLC system. Column; Luna C-18, 4.6×75 mm, 3 u Mobile phase A; 100% H2O+0.05% TFA Mobile phase B; 100% CH3CN+0.05% TFA Gradient; 1% B to 95% B in 15 min, hold 95% B for 2 min Flow Rate; 1 mL/min Inj. Volume; 5 uL Detection; 255 nm Column temperature; 25 C. Retention times; (II) (7.04 min), (2) (9.70 min), (1) (10.73 min). 1H NMR (400 MHz, DMSO-d6) delta 9.85 (s, 1H), 8.20 (s, 1H), 7.39 (d, 1H, Ph, J=7.6 Hz), 7.28 (d, 1H, Ph, J=7.1 Hz), 7.24 (t, 1H, Ph, J=7.7 Hz), 6.01 (s, 1H), 3.43 (m, 4H, piperazine), 2.73 (m, 4H, piperazine), 2.39 (s, 3H, CH3), 2.23 (s, 3H, CH3) ES+ MS m/z (rel. intensity) 444 (MH+, 100)

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, 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Arora, Vinod Kumar; Christopher, Lisa Joy; Cui, Donghui; Li, Wenying; US2006/211705; (2006); A1;,
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Related Products of 1044145-59-6, Adding some certain compound to certain chemical reactions, such as: 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol,molecular formula is C6H7ClN2OS, 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 1044145-59-6.

To a solution of KR-i 8 (i .7 g, 9 mmol) in 0H2012 (20 mL) was added TBSCI(tert-Butyldimethylsilyl chloride) (2.0 g, i3.3 mmol), imidazole (i .2 g, i8mmol). The reaction mixture was stirred at r.t. for iO h. The reaction mixturewas quenched into water, extracted with 0H2012, dried with anhydrousNa2SO4, concentrated to give the crude product which was purified by column chromatography (eluting with PE/ EA = iOO:i to 5:i) to give the pure reagent KR-19 (2.1 g, 77.8%) as a yellow solid. ESI-MS (Mi-i): 305.1 calc. for C12H21CIN2OSSi: 304.0.

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. 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUNDACION PARA LA INVESTIGACION MEDICA APLICADA; CUADRADO TEJEDOR, Maria Del Mar; FRANCO FERNANDEZ, Rafael; GARCIA OSTA, Ana Maria; OYARZABAL SANTAMARINA, Julen; RABAL GRACIA, Maria Obdulia; WO2014/131855; (2014); A1;,
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Synthetic Route of 7752-82-1, 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below.

In the 500 ml round bottom flask in three adding 2 – amino -5 – bromo pyrimidine (10.44g, 60mmol), joint boric acidfrequency that alcohol ester (19.05g, 75mmol), acetonitrile 300 ml, potassium acetate (17.67g, 180mmol), Pd (dppf) Cl2.CH2Cl2 (2.45g, 3mmol). The mixture of the reaction bottle 85 C stirring for 6.5 hours. TLC and HPLC to determine the completion of reaction. After the reaction, steaming and to remove the solvent, to obtain crude product, crude methylene chloride: hexane=1:3 beating, then ethyl acetate recrystallization to obtain the pure product 2 – amino pyrimidine -5 – boric acid frequency which ester borate, after drying, calculating yield 80%, purity 99.45% (HPLC).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7752-82-1, its application will become more common.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Cheng Wei; Geng Xuanping; Wang Lei; Lai Xinsheng; Lai Chao; Lai Ziteng; (5 pag.)CN106632443; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)pyrimidine, 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, Safety of 2-(Tributylstannyl)pyrimidine, blongs to pyrimidines compound. Safety of 2-(Tributylstannyl)pyrimidine

EXAMPLE 889-Amino-2-cyclobutyl-5-pyrimidin-2-yl-2,3-dihydropyrrolo[3,4-b]quinolin-1-one9-amino-5-bromo-2-cyclobutyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (306 mg, 0.92 mmol), CombiPhos-Pd6 (46.1 mg, 0.09 mmol), 2-(tributylstannyl)-pyrimidine (680 mg, 1.84 mmol) and N,N-dicyclohexylmethylamine (252 mg, 1.29 mmol) in DMF (5 mL) were heated at 100 C. for 48 hours. Then, the reaction mixture was cooled to room temperature, diluted with methylene chloride (100 ml), washed with water, dried through magnesium sulfate and evaporated to dry. The crude product was purified by column chromatography three times eluted with 20-100% ethyl acetate in hexane, 0-100% CAN in chloroform and 0-5% methanol in methylene chloride to afford the title compound as a yellow solid (26 mg, 8.5%). 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 8.93 (d, J=4.9 Hz, 2 H) 7.96 (t, J=7.2 Hz, 2 H) 7.56 (dd, J=8.2, 7.3 Hz, 1 H) 7.33 (t, J=5.0 Hz, 1 H) 6.41 (br. s., 2 H) 4.90 (quintet, J=8.7 Hz, 1 H) 4.46 (s, 2 H) 2.19-2.30 (m, 4 H) 1.71-1.83 (m, 2 H). MS APCI, m/z=332.3 (M+H). HPLC 1.63 min.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
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Application of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

171 mg of compound c25-12 and 165 mg of compound b3-1 were dissolved in 13 mL of ethylene glycol monomethyl ether and 0.43 mL of ethanol, and 0.26 mL of a hydrogen chloride solution (5.6 M) was added thereto, and the mixture was reacted at 120 C for 18 hours.The solvent was removed under reduced pressure, water was added to PH 9 with potassium carbonate, extracted with dichloromethane, dried, concentrated, obtained by column chromatography 24mg compound c-25;

According to the analysis of related databases, 1197953-49-3, the application of this compound in the production field has become more and more popular.

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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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. 54535-00-1, name is (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Under ice bath, intermediate b3 (2.0 g, 11.0mmol) was solubilized in dichloromethane (10 mL). a solution ofthionyl chloride (12.0 mmol) in dichloromethane (10 mL) wasadded drop-wise. The mixture was stirred at rt for 3 h. After that,the solvent was removed under reduced pressure and ethyl acetatewas added, then the mixture was washed by saturated sodiumbicarbonate solution followed by brine, and dried with Na2SO4, filteredand evaporated in vacuo to get yellow solid (1.9 g, 89%). MS[M+H]+ m/z: 197.

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, 54535-00-1, (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol.

Reference:
Article; Liu, Moyi; Xu, Qiaoling; Guo, Su; Zuo, Ruixi; Hong, Yue; Luo, Yong; Li, Yingxiu; Gong, Ping; Liu, Yajing; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2621 – 2631;,
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Adding a certain compound to certain chemical reactions, such as: 125401-75-4, 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid, 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, Quality Control of 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid, blongs to pyrimidines compound. Quality Control of 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid

EXAMPLE 8 Ammonium 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (Compound No. 22) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid (5.1 g) and 28% aqueous ammonia (1.7 g) were mixed with a solvent mixture of THF/ethanol. Precipitated crystals were washed with acetone to obtain the above identified compound as white crystals (3.7 g). (Melting point: 135-140 C.

The synthetic route of 125401-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4906285; (1990); A;,
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Application of 3932-97-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 3932-97-6 as follows.

Step 1: To a solution of 60_1 (2.00 g, 9.22 mmol, 1.00 eq) in THF (40 mL) was added ZnCi2-Et20 (1 M, 11.06 mL, 1.20 eq) at 0C under nitrogen protection. The mixture was stirred for 2 hours at 0C. Methylsulfanylsodium (646.23 mg, 9.22 mmol, 02429524H5-01 – TO SS?.48 muL·, 1.00 eq) was added. The resulting mixture was stirred at 20C for 16 hours. TLC (pure PE) showed reactant 1 (Rf=0.5) consumed and product (Rf=0.3) formed. The mixture was quenched with 1M HC1 (20 mL) and concentrated. The aqueous layer was extracted with DCM (20 mL*3). The combined organic layer was concentrated and purified by silica gel column (PE: EA=1 :0~50: 1) to give 60_2 (1.00 g, 1.97 mmol, 21.4% yield, 45.1% purity) as colorless oil. LCMS: RT = 0.794 min, mlz 228.9 [M+H]+ NMR (CDC13, 400 MHz) delta 8.67 (s, 1H), 2.62 (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,3932-97-6, its application will become more common.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (2017); A1;,
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