Day: January 27, 2021

Electric Literature of 4595-59-9, 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.4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, molecular weight is 158.984, as common compound, the synthetic route is as follows.

General procedure: Method A: K3PO4 (531 mg, 2.5 mmol) was added to a solution of 5-bromopyrimidine (1) (159 mg, 1.0 mmol), phenylboronic (2a)[2-fluorobenzeneboronic acid (2b), 3-fluorobenzeneboronic (2c), 4-fluorobenzeneboronic (2d), 2,4-difluorobenzeneboronic (2e), 3,5-difluorobenzeneboronic (2f), 2-(trifluoromethyl)benzeneboronic (2g), 3-(trifluoromethyl)benzeneboronic (2h), 4-(trifluoromethyl)benzeneboronic (2i), 2,4-bis(trifluoro-methyl)benzeneboronic (2j), or 3,5-bis(trifluoro-methyl)benzeneboronic (2k) acids] (1.2 mmol) and trans-bis(dicyclohexylamine)palladium(II) acetate (29 mg, 0.05 mmol) in EtOH (10 mL). The resulting suspension was stirred at ambient temperature for 24 h. EtOH wasevaporated under a reduced pressure and the residue was suspendedin CH2Cl2 (20 mL) and filtered from inorganic salts. After that solvent was distilled off under a reduced pressure, and theresidue was purified by flash column chromatography on silicagel (hexane/ethyl acetate, 1:3) to afford the desired cross-coupling products (3a-k).

Statistics shows that 4595-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyrimidine.

Reference:
Article; Verbitskiy, Egor V.; Baskakova, Svetlana A.; Kravchenko, Marionella A.; Skornyakov, Sergey N.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N.; Bioorganic and Medicinal Chemistry; vol. 24; 16; (2016); p. 3771 – 3780;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 161489-05-0, 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 161489-05-0, name is 4-Iodo-6-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of(S)-4-(difluoromethyl)-N-(6-(3,4-dimethylpiperazin-1- yl)-2,4-difluoro-3 -(1,2,3 ,6-tetrahydropyridin-4-yl)phenyl)-6-oxo- 1 ,6-dihydropyridine- 3-carboxamide (31.5 mg, 0.064 mmol, preparation described in Example 34) and 2- bromo-5-methoxypyrimidine (16.89 mg, 0.089 mmol) in 2-propanol (2.5 mL) at RT was added N,N-diisopropylethylamine (0.022 ml, 0.128 mmol). After heating in a microwave reactor at 170 C for 2 h, the reaction mixture was purified on preparatory column eluting with water (containing 0.1% HCOOH)/acetonitrile (containing 0.1% HCOOH) gradient (85/55). The title compound was isolated as an yellow powder (20 mg, 50%). LCMS [M+1j 602.5.

According to the analysis of related databases, 161489-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6153-44-2, Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, 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: Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, blongs to pyrimidines compound. Recommanded Product: Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Methyl orotate (20.0 g, 118 mmol) was combined with iodine (12.8 g, 50 mmol) and periodic acid (4.8 g, 21 mmol) in methanol (250 mL) and heated at reflux for 20 h. After cooling to ambient temperature, the volatiles were removed by rotary evaporation. The solid residue was slurried in water, collected by filtration, washed well with water and dried under vacuum at 70¡ã C. to provide the title compound (34 g, 97percent yield) as a solid. It was used without further purification. MS: m/z=296.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6153-44-2, Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; US2009/88322; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1004-39-3 ,Some common heterocyclic compound, 1004-39-3, molecular formula is C4H6N4S, 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.

PREPARATION 6 Synthesis of 4,6-diaminopyrimidine 167.78 g of 2-mercapto-4,6-diaminopyrimidine was dissolved in 1007 ml of 1.5N-aqueous sodium hydroxide solution, and the reaction solution was cooled down to 0 to 4 C. To this reaction solution was slowly added dropwise 267.55 g of 30% aqueous hydrogen peroxide solution. After the addition is completed, 170 ml of acetic acid was slowly added dropwise to the reaction solution to precipitate the solid product which was then filtered, washed successively with 200 ml of distilled water, 200 ml of methanol and 400 ml of diethylether and dried to obtain 185.56 g of the solid product as a white powder. The solid product thus obtained was slowly added to 1 L concentrated hydrochloric acid which was cooled to 0 C. to 4 C. The reaction solution was stirred for one hour at the same temperature, warmed to room temperature and then stirred for further 8 hours. The solid product produced during the reaction was filtered, washed with 1 L of acetone and 1 L of diethylether and then dried to obtain 109.13 g of the title compound in the form of hydrochloride salt. 109.13 g of the solid thus obtained was suspended in 400 ml of distilled water, and 200 ml of 15% aqueous sodium hydroxide solution was then added thereto. The mixture was stirred at room temperature for one hour and filtered. The filtered solid product was washed with 400 ml of ethanol and then dried to obtain 100.7 g of the title compound as a white powder. NMR (delta, DMSO-d6): 5.34(s, 1H), 6.01(s, 4H), 7.78(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Patent; Lucky, Ltd.; US5541175; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
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. 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