Day: May 18, 2021

Application of 5466-43-3 ,Some common heterocyclic compound, 5466-43-3, molecular formula is C7H6Cl2N2, 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.

Morpholine (0.32 mL, 3.7 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.5 g, 2.65 mmol) in anhydrous ethanol (5 mL) and stirred at a temperature in the range of 65 C. to 85 C. for 10 to 16 hours. Thereafter, the mixture was concentrated under reduced pressure and the crude was diluted with anhydrous ether. After standing at a temperature in the range of 5 C. to 10 C. for 2 hours, the precipitated solid was filtered and washed with ether. The solid was recrystallized from ethyl acetate to afford the title compound as a pale yellow solid (0.54 g, 86% yield).1H NMR (CDCl3, 300 MHz): delta 4.10-3.94 (m, 4H), 3.90-3.76 (m, 4H), 3.36-3.20 (m, 2H), 3.10-2.90 (m, 2H), 2.29-2.12 (m, 2H).LC-MSD (ES+): (m/z) 240 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-65-8, 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 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-((4-bromo-2-fluorophenoxy)methyl)piperidine hydrochloride (5.6 g, 17.3 mmol) in dimethylformamide (20 mL) was added 2-chloro-5-methoxypyrimidine (2.7 g, 19.0mmol) and diisopropylethylamine (5.6 g, 43.3 mmol). The reaction mixture was stirred and heated in “CEM” microwave system (140C, 17 hours). Upon completion, the reaction mixture was poured into water (100 mL). A precipitate was filtered, air-dried and purified by column chromatography eluting with hexanes: ethyl acetate mixture (9: 1) to afford the title compound as a yellow solid (2.9 g, 42 %).

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 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
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.51940-63-7, name is Ethyl 6-chloropyrimidine-4-carboxylate, molecular formula is C7H7ClN2O2, molecular weight is 186.5957, as common compound, the synthetic route is as follows.Quality Control of Ethyl 6-chloropyrimidine-4-carboxylate

Tripotassium phosphate (1.12 g, 5.63 mmol) was added in one portion to a stirred solution of 2-(2H-l,3-benzodioxol-5- yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.93 g, 3.75 mmol) and ethyl 6- chloropyridine-4-carboxylate (0.7 g, 3.75 mmol) in DMF (20 mL). The mixture was degassed with nitrogen for 5 minutes, after which time Pd(dppf)2C12 (0.14 g, 0.19 mmol) was added in one portion, the mixture was then heated to 80oC and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (200mL) and water (lOOmL). The organic layer was separated, washed sequentially with water (lOOmL) then brine (lOOmL) before being dried (MgS04), filtered and concentrated. The resulting brown solid was purified by flash column chromatography (elution: 40%EtOAc, 60%) Heptane) to give the desired compound (0.31 g, 31% yield) as a white solid. Tr = 1.87 min m/z (ES+) (M+H+) 273.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51940-63-7, Ethyl 6-chloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; COURTNEY, Stephen Martin; PRIME, Michael; MITCHELL, William; BROWN, Christopher John; DE AGUIAR PENA, Paula C.; JOHNSON, Peter; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia M.; MUNOZ, Ignacio; WO2013/33085; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H9N3

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

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, 767-15-7, 2-Amino-4,6-dimethylpyrimidine.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3993-78-0, 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.3993-78-0, name is 2-Amino-4-chloropyrimidine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.

A mixture of 2-amino-4-chloro-pyrimidine (7,5 mmol, 1g) with DMAP (0,2 eq, 1,5 mmol, 183,5 mg), triethylamine (0,2 eq, 1,5 mmol, 0,2 ml) and di-tert-butyl-dicarbonate (2 eq, 15 mmol, 3,2 g) in dichloromethane (60 mL) was stirred at room temperature for 48 h. When the reaction was finished the solvent is evaporated and the resulting crude was dissolved in CH2Cl2 and washed with water. The organic phase was evaporated to dryness in vacuo and the residue purified by silica gel column chromatography using as eluent AcOEt/Heptane in gradient. NMR (CDCl3): delta ppm 7.9 (d, 1H); 6.52 (d, 1H); 1.43 (s, 18 H)

The chemical industry reduces the impact on the environment during synthesis 3993-78-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOSCIRA, S.A.; Medina Padilla, Miguel; Dominguez Correa, Juan Manuel; Fuertes Huerta, Ana; Palomo Nicolau, Francisco; Lopez Ogalla, Javier; Herrero Santos, Susana; Alonso Cascon, Mercedes; Alonso Gordillo, Diana; Rubio Arrieta, Laura; EP2647634; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1558-17-4 ,Some common heterocyclic compound, 1558-17-4, molecular formula is C6H8N2, 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.

General procedure: Preparation of 1a’-3f’ and 1g-5g. A mixture of pyrimidines (2.00 mmol) and benzaldehydes (4.00 mmol) in 5 N NaOH solution (20 mL) containing tetrabutylammonium hydrogen sulfate (0.10 g, 0.29 mmol) was refluxed. After cooling, the precipitates were filtered off. The products were purified by recrystallization from EtOAc. Otherwise, the mixture was extracted with CH2Cl2. Then, the organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography to give the products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1558-17-4, its application will become more common.

Reference:
Article; Lee, Yun Suk; Kim, Hye Yun; Kim, Youngsoo; Seo, Jae Hong; Roh, Eun Joo; Han, Hogyu; Shin, Kye Jung; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 4921 – 4935;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 444731-75-3, 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.444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, molecular weight is 287.75, as common compound, the synthetic route is as follows.

Example 69 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide To a solution of Intermediate Example 13 (200 mg, 0.695 mmol) and 5-amino-2-methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of conc. HCl. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. HCl salt of 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1H), 8.55 (br s, 1H), 7.81 (d, J = 6.2 Hz, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.69 (m, 1H), 7.43 (s, 1H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1H), 6.86 (m, 1H), 5.74 (d, J = 6.1 Hz, 1H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

Statistics shows that 444731-75-3 is playing an increasingly important role. we look forward to future research findings about N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; Novartis AG; Boloor, Amogh; Cheung, Mui; Davis, Ronda; Harris, Philip Anthony; Hinkle, Kevin; Mook, Robert Anthony Jr; Stafford, Jeffery Alan; Veal, James Martin; EP2311825; (2015); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, 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. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below.

Step Y1 : 2-(5-Bromo-4-methoxy-pyrimidin-2-ylamino)-ethanol A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (5 g, 22.4 mmol) and 2-amino ethanol (1.76 mL, 29.1 mmol) in THF (50 mL) was stirred for 18 h at rt. 2-Amino ethanol (2 mL) was added. The reaction mixture was stirred for 18 h at rt and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 3:2) to afford 4.08 g of the title compound. tR: 0.70 min (LC-MS 2); ESI-MS: 248.2 [M+H]+ (LC-MS 2); Rf: 0.06 (hexane/EtOAc 3:2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5305-59-9 , The common heterocyclic compound, 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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.

To a solution of 6-chloropyrimidin-4-amine (500 mg) and N,N-dimethylaminopyridine (47.2 mg) in acetonitrile (5.0 mL) was added di-tert-butyl dicarbonate (2.24 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 days, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.13 g). MS (ESI+) : [M+H]+330.2

The synthetic route of 5305-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 26032-72-4, Adding some certain compound to certain chemical reactions, such as: 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine,molecular formula is C10H6Cl2N2, 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 26032-72-4.

The compound 2,4-dichloro-6-phenylpyrimidine (1.52 g, 6.7 mmol),(+/-)-trans-3-aminobicyclo[2.2.2]octane-2-carboxylic acid methyl ester(1.84 g, 10.0 mmol) was dissolved in N,N-dimethylformamide (10 mL).Potassium carbonate (0.92 g, 6.7 mmol) was then added to the reaction mixture.The resulting mixture was stirred at room temperature overnight. After the reaction is complete,It was diluted with H2O (50 mL), and the mixture was extracted with ethyl acetate (40mL×3).The combined organic phases were washed with saturated brine (50 mL).Dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was purified by silica gel column chromatography(n-hexane/ethyl acetate (v/v) = 20/1-10/1)The title compound was obtained as a white solid(1.65g, 66%).

According to the analysis of related databases, 26032-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia