Pyrimidines

Reference of 705263-10-1, Adding some certain compound to certain chemical reactions, such as: 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine,molecular formula is C6H4BrN3, 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 705263-10-1.

The intermediate of formula VI (30 mmOl, 5.9 g)And the substance of formula VII (30 mmol, 4.6 g)Was placed in a 250 ml round bottom flask equipped with a reflux condenser, potassium carbonate (90 mmol, 12.4 g) and Pd (PPh3) 4 (3 mmol, 3.3 g) were added, dioxane (90 ml) and water (30 ml ), Stirred under nitrogen for three times, heated under nitrogen to 110 C, stirred for 4 h,After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The mixture was extracted with 100 ml of water and 100 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted with dichloromethane 50 ml chi 3 for 3 times. Dried over sodium sulfate, the solvent was removed by suction filtration, and the residue was purified by column chromatography with ethyl acetate / petroleum ether to give 5.5 g of a pale yellow product.The pale yellow product is an intermediate of formula III-1,The yield of the intermediate of formula III-1 was calculated to be 82%.

According to the analysis of related databases, 705263-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Zhipulai Bio-pharmaceutical Technology Co., Ltd.; Chen Wei; Zhao Gang; Pu Lin; Liu Jifeng; (13 pag.)CN105130991; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 113583-35-0, 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.113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, molecular weight is 218.23, as common compound, the synthetic route is as follows.

Process for producing 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-methylaminopicolinic acid (Second method) 10.5 mg (0.0576 mmol) of methyl 6-methylamino-3-hydroxypicolinate, 11.6 mg (0.0532 mmol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine, 8.8 mg (0.637 mmol) of potassium carbonate and 0.5 ml of dry dimethylsulfoxide were mixed. The mixture was stirred at room temperature for 5 hours, and then a 10% potassium hydroxide aqueous solution (corresponding to 90 mg, 0.160 mmol) was added thereto. The mixture was reacted at room temperature for one hour, and then 2.0 ml of water was added to the reaction mixture. Further, 1.0 ml of a 10% citric acid aqueous solution was added thereto, and the mixture was left to stand, whereby crystals precipitated. After being thoroughly precipitated, the crystals were filtered under suction and washed with water. The crystals were dried to obtain 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-methylaminopicolinic acid. Colorless prism crystals, 13.7 mg (yield: 84.0%)

The chemical industry reduces the impact on the environment during synthesis 113583-35-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP567133; (1993); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 46155-89-9, 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, 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, Recommanded Product: 46155-89-9, blongs to pyrimidines compound. Recommanded Product: 46155-89-9

A solution of 1 g (5.58 mmol)of compound 1a in 5 mL of concentrated sulfuric acid was cooled to 2-5C, and a mixture of 0.37 mL(5.58 mmol) of nitric acid (d = 1.41 g/cm3) and 2 mL of concentrated sulfuric acid was added dropwise with vigorous stirring and cooling. The mixture was stirred for 1 h and poured onto 20 g of ice. After 30 min, the precipitate was filtered off and washed with 10 mL of water. Yield 0.77 g (62%, assuming formation of mononitro derivatives). According to the 1H NMR data, the product was a mixture of 6- and 7-nitro derivatives ata ratio of 7 : 93. It was recrystallized from 55 mL of ethanol to isolate 0.47 g (38%) of 7-nitro isomer 2a,mp 272-273C. IR spectrum, nu, cm-1: 3150 m (NH),1710 s, 1680 s (C=O), 1575 s, 1390 s (NO2). 1H NMRspectrum (DMSO-d6), delta, ppm: 3.25 s (3H, 1-CH3),3.58 s (3H, 3-CH3), 8.27 d (1H, 6-H, J = 3.47 Hz),13.55 br.s (1H, NH). Found, %: C 42.73; H 3.70;N 24.88. C8H8N4O4. Calculated, %: C 42.86; H 3.60;N 24.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,46155-89-9, 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Tkachenko, Yu. N.; Popov; Pozharskii; Borodkin; Levchenkov; Russian Journal of Organic Chemistry; vol. 53; 10; (2017); p. 1564 – 1572; Zh. Org. Khim.; vol. 53; 10; (2017); p. 1536 – 1543,8;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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. category: pyrimidines

To a stirred solution of 4-chloro-5-iodopyrimidine (300 mg, 1.248 mmol) in DMF (2 mL) was added cesium carbonate (813 mg, 2.496 mmol) and morpholine (0.435 mL, 4.99 mmol). The reaction was purged with N2, heated to 90 C for 12 hours and then concentrated to give the crude Intermediate 44, which was used directly in subsequent reaction. MS (ES): m/z = 292.1 [M+H]+. ‘H NMR (400 MHz, MeOD) delta ppm 8.69 (1 H, s), 8.56 (1 H, s), 3.76-3.86 (5 H, m), 3.61-3.71 (5 H, m). Intermediate 44 was used in the synthesis of Example 224.

With the rapid development of chemical substances, we look forward to future research findings about 63558-65-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AUSTIN, Joel, Francis; SHARMA, Lisa, S.; BALOG, James, Aaron; HUANG, Audris; VELAPARTHI, Upender; DARNE, Chetan, Padmakar; SAULNIER, Mark, George; WO2012/15723; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]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, Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

General Procedure 7 Step 2: Methyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate; To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15 g, 64.377 mmol) in THF (378 ml.) n-BuLi (1.4 M in hexanes, 96.56 ml_, 135.19 mmol) is added dropwise at -78 0C. The reaction solution is stirred for 30 min and then methyl chloroformate (4.73 ml_, 61.15 mmol) in THF is added at -78 0C and the reaction mixture is allowed to attain room temperature and is stirred for 3 h. The reaction is quenched with aq. NH4CI. The solvent is distilled off and the residual solution is extracted with EtOAc (3 x 300 ml_). The combined organic layer is washed with water (300 ml_), brine (300 ml_), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue is purified by column chromatography to give methyl 4-chloro-7H- pyrrolo[2,3-d]pyrimidine-5-carboxylate as a pale yellow solid.1H-NMR (400 MHz, DMSO-d6): delta 13.3 (brs, 1 H), 8.69 (s, 1 H), 8.42 (s, 1 H), 3.82 (s, 1 H). ESI- MS (pos.): 21 1.8 (M+H).

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Yen Liang; DURAISWAMY, Jeyaraj; HALLER, Sarah; KEIM, Matthias; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15643; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 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-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, blongs to pyrimidines compound. Quality Control of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

Example 4.Preparation of the isoamyl alcohol solvate (SI) of dasatinib:The intermediate of formula II (0.42 g; 1.07 mmol), l-(2-hydroxyethyl)piperazine (0.8 g; 6.15mmol) and diisopropylethylamine (0.38 ml, 2.18 mmol) were suspended in isoamyl alcohol (7ml) under an inert atmosphere. The reaction mixture was stirred and heated up to 140C for 6hours. The reaction mixture was withdrawn from the heating bath and stirred intensively. Crystallization started at the inner temperature of 95C, the suspension was left to cool under continuous stirring. After achieving the laboratory temperature it was stirred for another 2 hours. The crystalline substance was aspirated on fit S3, washed with isoamyl alcohol (7 nil)and dried at the laboratory temperature in vacuo (2.5 kPa) for 5 hours. The yield was 0.5 g;81% of the theoretical yield. FIPLC purity 99.10%. The XRPD pattern corresponds to the isoamyl alcohol solvate (SI). The SI solvate is characterized by the reflections presented in Table 2:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ZENTIVA, K.S.; ZELENKA, Karel; HAJICEK, Josef; DAMMER, Ondrej; WO2014/86326; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14394-70-8, 2-Chloro-5-methylpyrimidin-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, 14394-70-8, blongs to pyrimidines compound. Formula: C5H6ClN3

[0293] A mixture of l-bromo-3,5-dimethoxybenzene (436 mg, 2.01 mmol), 2-chloro~5- methyl-pyrimidin-4-ylamine (287 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), Xantphos (237 mg, 0.41 mmol) and potassium fe/t-butoxide (448 mg, 3.99 mmol) in dioxane (15 mL) and DMF (5 mL) was microwaved at 160 C for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow solid (182 mg, 33%).[0294] 1H NMR (500 MHz, DMSO-d6): delta 2.17 (s, 3H), 3.74 (s, 6H), 6.27 (t, J= 2.2 Hz, IH), 6.99 (d, J=2.2 Hz, 2H), 8.06 (s, IH), 8.71 (s, IH). MS (ES+): m/z 280 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14394-70-8, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 64224-60-8, 5-Bromo-4-pyrimidinecarboxylic 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, 64224-60-8, blongs to pyrimidines compound. SDS of cas: 64224-60-8

5-bromopyrimidine-4-carboxylic acid (prepared according to the procedure described in U.S. Pat. No. 4,110,450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH2Cl2 (100 ml). Oxalylchloride (1.1 eq, 2.9 ml, 33.0 mmol) was added followed by 2 drops of DMF. The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The residue was taken in MeOH (50 ml) and heated. After evaporation of MeOH in vacuo the compound was dissolved in CH2Cl2 and poured on a prepacked silica gel column. The material was eluted using 20% Ethyl acetate in hexanes. Evaporation of the solvent provided methyl-5-bromopyrimidine-4-carboxylate as a light orange crystalline solid (2.54 g, 39% yield). LCMS (ES): 95% pure, m/z 217 [M]+; 219 [M+2]+; 1H NMR (CDCl3, 400 MHz) delta 4.04 (s, 3H), 9.02 (s, 1H), 9.21 (s, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64224-60-8, its application will become more common.

Reference:
Patent; CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P.; US2009/239859; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3764-01-0, 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. 3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, 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 solution of iotaetaomicronphietaomicronetabeta (100 g; 1.15 moles; 5.3 equivalents) in THF (450 mL) was cooled with an ice bath. A solution of 2,4,6-trichloropyrimidine (39.9 g; 217 mmoles; 1.0 equivalents) in THF (100 mL) was added over a period of 30 minutes. A copious white precipitate formed upon addition of 2,4,6-trichloropyrimidine and the reaction mixture rapidly thickened. The mixture was allowed to warm to ambient temperature and mechanically stirred for 64 hours (heating the reaction mixture at reflux following the addition of 2,4,6-trichloropyrimidine leads to complete reaction in 60 min. The ratio of a to b was unchanged). The mixture was then filtered and the filter cake washed with additional THF (2 x 100 mL). The filtrate was concentrated on the rotavap. Water (600 mL) was added and the resulting slurry was stirred for 30 minutes. The solids were isolated by filtration, washed with additional water (2 x 100 mL) and dried overnight under vacuum. Yield a + b: 61.3 g (99%). Product was 87% a by hplc area percent; remainder is b.[00128] 31 g of the crude solid was dissolved in 200 mL of CH2CI2 and applied to 600 g of dry silica in a fritted glass funnel. The silica was eluted with 1 : 1 hexane : EtOAc and 300 mL fractions were collected. TLC analysis shows a to be present in fractions 1 -7 and 4,6- dimo holino-2-chloropyrimidine in fractions 6-10. Fractions 1-5 were pooled and concentrated to provide a white solid. Yield: 28.2 g (Product was 98% a by hplc area percent).

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.74356-36-8, name is 2,4-Dimethyl-pyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.Quality Control of 2,4-Dimethyl-pyrimidine-5-carboxylic acid

110 mg (0.72 mmol) of 2,4-dimethyl-pyrimidine-5-carboxylic acid and 215 mg (0.57 mmol) of O-(benzotriazol-1-yl)N,N,N’,N’-tetramethyluronium-hexa-fluorophosphate are dissolved in 4 mL of N,N-dimethylformamide and 62 muL (0.57 mmol) of 4-methyl-morpholine are added. The mixture is stirred for 10 min and a solution of 170 mg (0.47 mmol) [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester and 102 muL (0.57 mmol) of di-iso-propylethylamine in 4 mL of N,N-dimethylformamide is added. The reaction mixture is stirred for 2 h at room temperature, and diluted with ethyl acetate. The organic layer is washed with brine, saturated sodium bicarbonate solution and brine, dried with sodium sulfate, filtered and concentrated in vacuo to yield the title compound. LC/MS (I) (5-95%, 5 min): rt 3.89 min; m/z 437, 493 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74356-36-8, 2,4-Dimethyl-pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; BIOVITRUM AB; EP2019099; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia