Pyrimidines

Reference of 4595-61-3, 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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.

Step 10: Preparation of N-r7-methoxy-8-(3-morpholin-4-ylpropoxy)-2.3- dihvdroimidazopi ^-ciquinazolin-S-vnpyrimidine-delta-carboxamide .; 7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1 ,2-c]quinazolin-5-amine (100 mg, 0.22 mol) was dissolved in DMF (5 ml_), and pyrimidine-5-carboxylic acid (41 mg, 0.33 mmol) was added. PYBOP (173 mg, 0.33 mmol) and diisopropylethylamine (0.16 ml_, 0.89 mmol) were subsequently added, and the mixture was stirred at rt overnight. EtOAc was added, and the precipitate was isolated by vacuum filtration to give the title compound (12 mg, 11percent): HPLC MS RT = 1.07 min, MH+= 466.2; 1H NMR (DMSO-cfe + 2 drops TFA-cQ delta: 9.48 (2H, s), 9.39 (1 H, s), 8.05 (1 H, d), 7.47 (1 H, d), 4.59 (2H, m), 4.35 (2H, br t), 4.26 (2H, m), 4.02 (3H, s), 4.00 (2H, m), 3.67 (2H, br t), 3.52 (2H, m), 3.33 (2H1 m), 3.16 (2H, m), 2.27 (2H, m).

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 4595-61-3, Pyrimidine-5-carboxylic acid.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2008/70150; (2008); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 90213-66-4, 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 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

2,4-Dchloro-7H-pyrrolo[2,3-d]pyrimidine (5.0 g, 27 mmol) was suspended in MeCN (300 mL) and AcOH (60 mL); to this was added selectfluor (1-chloromethyl-4-fluoro-1 ,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 1.4 eq, 13.2 g) in one portion. The reaction mixture was stirred at 60 C overnight. HPLC monitoring indicated complete conversion. After the solvents were evaporated to the volume of -100 mL, toluene (20 mL) was added and the suspension was filtered. The filtrate was evaporated to dryness and re-evaporated with toluene (2 chi 20 mL). The residue was then purified via a short silica pad (washing with 1/1 DCM/EtOAc) and column chromatography (ISCO machine, EtOAc/DCM, EtOAc on a 0-100% gradient) to give the crude product. Upon standing the pure product was seen to precipitate from the column fractions. These were filtered and the mother liquors were combined to precipitate a 2nd crop. Total 1.23 g of the product 64 was obtained (22% yield, ~ 90% pure, Cl-isomer was the main impurity).

According to the analysis of related databases, 90213-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZHU, Xiaotian; WANG, Yihan; SHAKESPEARE, William, C.; HUANG, Wei-Sheng; DALGARNO, David, C.; WO2013/169401; (2013); A1;,
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Pyrimidine – Wikipedia

Reference of 75833-38-4 , The common heterocyclic compound, 75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

a) 2-Chloropyrimidine-4-carboxamide 338 g of 98% strength formic acid are introduced into a 1–1 round bottom flask fitted with magnetic stirring and containing 131.9 g (946 mmol) of 2-chloropyrimidine-4-carbonitrile, and a stream of gaseous hydrochloric acid is passed through slowly for 1 h 30 min. The mixture is allowed to stand overnight, the solid is isolated on sintered glass and is then purified by recrystallisation with filtration while hot, from a mixture of nitromethane and ethyl acetate. In this way, 107.03 g of grey solid are isolated as three crops, after drying under vacuum and with heating. Melting point: 152.5-154 C.

The synthetic route of 75833-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5164397; (1992); A;,
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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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, 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: C14H17ClN4O

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

With the rapid development of chemical substances, we look forward to future research findings about 1211443-61-6.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 93366-88-2, 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 93366-88-2 as follows.

The final product 03 (20 mg, 0.062 mmol), 2-amino-7H-pyrrolo [2,3-d] pyrimidine (25 mg, 0.186 mmol) and Et3N (25 mg, 0.25 mmol) were weighed into a bottle,Add 2 mL of DMF to dissolve the reaction reagent.The reaction was heated at 50 C overnight.The crude reaction product was directly purified by reverse-phase HPLC to obtain the target compound YC124 (18.8 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,93366-88-2, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
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. 1074-41-5, name is 6-Amino-2-(methylthio)pyrimidin-4-ol, molecular formula is C5H7N3OS, 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. Quality Control of 6-Amino-2-(methylthio)pyrimidin-4-ol

General procedure: A mixture of equimolar amounts of 6-amino-2-(methylthio)pyrimidin-4(3H)-one (1) (1 mmol), ethylcyanoacetateor meldrum?s acid (2 or 5) (1 mmol) and aldehyde(3 or 6) (1 mmol) was added to a vial containinga magnetic stirring bar and [DMBSI]HSO4 (0.18 mmol,0.06g) and heated at 80 C in an oil bath. Stirring at 80C was continued until disappearance of the startingmaterials. At this stage, due to the poor solubility in theionic liquid, the product appears as a precipitate. Thereaction mixture was cooled and washed with water toextract the ionic liquid. The solid obtained was recrystallizedfrom ethanol to furnish the desired pure product.The ionic liquid was recovered from the aqueous extractsby evaporation under reduced pressure, and reusedin the next run.

With the rapid development of chemical substances, we look forward to future research findings about 1074-41-5.

Reference:
Article; Nia, Roghayeh Hossein; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Shirini, Farhad; Rassa, Mehdi; Acta Chimica Slovenica; vol. 60; 4; (2013); p. 889 – 895;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 171178-47-5, 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 171178-47-5 as follows.

COMPOUND EXAMPLE 16 Trans-4- [6- (4-HYDROXY-3-METHOXY-BENZYLCARBAMOYL)-4-OXO-4H-PYRIDO [3,4- d] pyrimidin-3-ylmethyl] -cyclohexanecarboxylic acid Step (a): 4-oxo-3, 4-dihydro-pyrido [3, 4-D] PYRIDINE-6-CARBOXYLIC acid methyl ester A solution of 6-chloro-3H-pyrido [3,4-d] pyrimidin-4-one (20.76g, 114. 3mmol), in 350mL of methanol was treated with triethylamine (39.8mL, 286MMOL), and dppf-PdC12 (1.87g, 2. 29MMOL), and the mixture was heated at 100C under 500psi of CO for 14 hours. The reaction mixture was cooled to room temperature. The resulting solid was collected by filtration, washed with methanol, washed with ethyl acetate, and dried to give 20.72g of 4-oxo-3,4- dihydro-pyrido [3, 4-D] PYRIDINE-6-CARBOXYLIC acid methyl ester as a gray solid (88. 3% yield). 1H NMR (400 MHz, DMSO-D6) delta (ppm) 3.9 (s, 3H), 8.3 (s, 1H), 8.5 (s, 1H), 9.1 (s, 1H), 12.8 (bs, 1H) MS (APCI) M + 1 = 206. 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171178-47-5, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/16926; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, 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 2,4-Dichloro-6-methyl-5-nitropyrimidine, blongs to pyrimidines compound. Safety of 2,4-Dichloro-6-methyl-5-nitropyrimidine

2,4-Dibenzyloxypyrrolo[3,2-d]pyrimidine was prepared by the method used for the preparation of 2,4-dimethoxypyrrolo[3,2-d]pyrimidine as described in Cupps, T. L., Wise, D. S. and Townsend, L. B. J. Org. Chem., 1983, 48, 1060-1064 and references therein. A solution of sodium benzoxide was prepared by adding sodium (4.5 g) to benzyl alcohol (100 ml) and heating under argon with stirring until all the sodium had reacted. This was added slowly to a solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (17 g) in benzyl alcohol (80 ml). When the exothermic reaction was complete, ether (500 ml) was added and the resulting solution was washed with water, dried (MgSO4), and evaporated, excess benzyl alcohol being removed by distillation under high vacuum. Dimethylformamide dimethyl acetal (25 ml) was added to a solution of the crude residue in dry DMF (100 ml). The resulting solution was heated at 100 C. for 3 h, then evaporated to dryness under high vacuum. The solid residue was triturated with hot ethanol, cooled and filtered to yield 2,4-dibenzyloxy-6-(2-dimethylaminoethenyl)-5-nitropyrimidine as an orange solid (24.5 g). A suspension of this product (20 g) in acetic acid (300 ml) was stirred with zinc dust (30 g), the reaction being cooled in an ice-bath during an exothermic reaction, when the reaction temperature rose to 50 C. The reaction mixture was allowed to attain room temperature for 2 h, and was then filtered, evaporated and partitioned between chloroform and aqueous bicarbonate. The organic phase was washed with water, dried (MgSO4) and evaporated to give 2,4-dibenzyloxypyrrolo[3,2-d]pyrimidine as a solid (15.2 g).

The synthetic route of 13162-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Industrial Research Limited; Albert Einstein College of Medicine of Yesheva University; US6693193; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)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, Formula: C5H5ClN2S, blongs to pyrimidines compound. Formula: C5H5ClN2S

The crude compound 3 (3.52 mmol) obtained from the previous step was dissolved in DCM (14 ml) and cooled to -5 C. A solution of m-CPBA (1.214 gm) in DCM (14 ml) was added drop wise to the solution of compound 3 at -5C over a period of 30 min. After complete addition, the reaction mixture was allowed to stir at room temperature (RT) for 15 h. On appearance of the white precipitate, it was filtered and washed with cold DCM. The filtrate was washed with 10% K2CO3twice and was dried over anhydrous Na2S04. The solvent was removed to obtain compound 4 as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49844-90-8, 4-Chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PANDA, Koustubh; NAGPAL, Latika; RANU, Brindaban C.; (45 pag.)WO2018/92034; (2018); A1;,
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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine, molecular formula is C4H2BrClN2, 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. SDS of cas: 32779-36-5

Example III-4 In an autoclave, N,N-dimethylamine hydrochloride (2.04 g, 25 mmol), potassium carbonate (6.91 g, 50 mmol), 5-bromo-2-chloropyrimidine (4.35 g, 22.50 mmol) and toluene (25 ml) are heated at 110 C. (bath temperature) for 20 hours. Ethyl acetate (50 ml) is added to the reaction mixture, and the organic phase is then washed with water (2*50 ml), dried over sodium sulphate, filtered and concentrated. This gives 4.01 g (72% of theory) of N-(5-bromo-2-pyrimidinyl)-N,N-dimethylamine. HPLC: log P (pH 2.3)=2.20 (purity: 91%) m.p. 68-69 C.

With the rapid development of chemical substances, we look forward to future research findings about 32779-36-5.

Reference:
Patent; Plant, Andrew; Seitz, Thomas; Jansen, Johannes Rudolf; Erdelen, Christoph; Turberg, Andreas; Hansen, Olaf; US2004/82586; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia