Tag: M.W=300-400

Electric Literature of 1197953-49-3 ,Some common heterocyclic compound, 1197953-49-3, molecular formula is C12H12Cl2N3OP, 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.

AP26113 intermediate (2g, 6.3mmol) was added sequentially in a standard microwave reaction tube at room temperature.SIAIS 1197129 (2.4 g, 7.8 mmol), Pd(OAc) 2 (176 mg, 0.78 mmol), Xantphos (810 mg, 1.4 mmol),cesium carbonate (6.4 g, 19.6 mmol), 30 mL DMF, followed by argon exchange, microwave reaction at 110 C for 1.5 h. TLC detection reactionAfter the bundle, the mixture was filtered through silica gel, water-purified, ethyl acetate, washed with water, dried over anhydrous sodium sulfate,Methanol and water gave a reddish brown solid (900 mg) directly to the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1197953-49-3, its application will become more common.

Reference:
Patent; ShanghaiTech University; Yang Xiaobao; Jiang Biao; Song Xiaoling; Lin Haifan; Sun Ning; Chen Jinju; Qiu Xing; Ren Chaowei; Kong Ying; (232 pag.)CN109912655; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 761440-16-8, Adding some certain compound to certain chemical reactions, such as: 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine,molecular formula is C13H13Cl2N3O2S, 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 761440-16-8.

Tert-butyl 4- (4-amino-5-isopropoxy-2-methylphenyl) piperidine-(0.300 g, 0.861 mmol),(0.298 g, 0.861 mmol), Pd [P (tBu) 3] 2 (0.044 g, 0.086 mmol) was added to a solution of 2,5-dichloro-N- (2- (isopropylsulfonyl) phenyl) pyrimidin-Mmol) and NaOtBu (0.083 g, 0.861 mmol) were mixed in toluene (5 mL), heated at 150 C for 20 minutes under microwave irradiation, and then cooled to room temperature to complete the reaction. The reaction mixture was poured into water and extracted with ethyl acetateAll. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 12 g cartridge; ethyl acetate / hexane = 0% to 30%) And concentrated to give tert-butyl 4- (4- (5-chloro-4- (2- (isopropylsulfonyl) phenylamino) pyrimidin- -methylphenyl) piperidine-1-carboxylate (0.252 g, 44.5%) as a lemon solid solid.

According to the analysis of related databases, 761440-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; YOO, CHUNG-YEOL; JIN, SEOK-MIN; KIM, JU-YOUNG; (34 pag.)KR2016/147358; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1421372-94-2, 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. 1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

Compound 6 (7.7 mL) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (compound 5, 15.5 g, 0.79) and K2CO3 (16.3 g) DMF (60 mL). The mixture was heated at 60 C. for 60 min and then water (150 mL) was added. Solids were filtered and rinsed with water. The crude dark red product was directly used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; X-Cutag Therapeutics, Inc.; CHENG, Changfu; WEN, Shuhao; LI, Hui Joyce; (30 pag.)US2019/169171; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. A new synthetic method of this compound is introduced below.

Compound 13 can then be obtained by treaUng compound 12 w[th TFA. Subsequent coupIng of compound 13 with compound 8 n the presence of DIPEA can afford compound 14.

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; COMBS, Colin; MULLER, Gerhard; DAMEN, Eddy; NAGAMOTO-COMBS, Kumi; (73 pag.)WO2017/100703; (2017); 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.Safety of (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

To a solution of methyl (E)-2-{2-[6-chloropyrimidin~4-yloxy]phenyl} -3-methoxyacrylate (64.4g; prepared as described in WO 92/08703) in cyclohexanone (approximately 80g) was added 2-cyanophenol (26.6g) and cyclohexanone (26.6g). The mixture was heated to 5O0C and DABCO (0.2g) in cyclohexanone (2g) and potassium carbonate (42.4g) were charged. The reaction was heated to 9O0C and held for three hours. The temperature was adjusted to 50-600C and hot water (88g) added, stirred for 15 minutes, and the aqueous phase separated. Analysis of the cyclohexanone layer gave a 91.3% yield of methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin). Cyclohexanone was removed by vacuum distillation, and to the distillation residues at 8O0C was added methanol (59g). The methanol solution was cooled slowly to 0-50C, filtered and the cake washed with methanol (2×15.8g) to give, after drying, methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (87.0% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
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.302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, molecular weight is 394.2783, as common compound, the synthetic route is as follows.Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methyl phenyl) thiazole- 5 -carboxamide compound of formula-2 (50 gm), 2-(piperazin-l-yl)ethanol compound of formula-3 (82.5 gm) & 1 ,2-propanediol (750 ml) is expelled with nitrogen for 30 minutes. N,N- diisopropylethylamine (43.6 ml) was added to the reaction mixture and heated the reaction mixture to 115-120C. Stirred the reaction mixture for 8 hours at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 6 hours at the same temperature. Filtered the precipitated solid and washed with 1 ,2-propanediol. Methanol (1300 ml) was added to the obtained wet compound and heated the reaction mixture to 65-70C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the reaction mixture at 65-70C and washed with methanol. Cooled the filtrate to 25-30C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with methanol and dried to get the title compound. Yield: 38 gm; HPLC Purity: 99.57%, 0.01% (N-Oxide impurity), 0.09% (Deshydroxyethyl dasatinib); PXRD pattern of the obtained compound depicted in figure-5.

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; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; KHALIL AHAMED, Mogal; (38 pag.)WO2017/2131; (2017); 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below., COA of Formula: C15H13ClN2O4

EXAMPLE 1 This Example illustrates the preparation of (E)-methyl 2-[2-(6-(2–cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (Compound No. 377 of Table I). (E)-Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.0 g), was treated with sodium methanethiolate (1.09 g) at room temperature in chloroform (15 ml) and water (10 ml) in the presence of a catalytic amount of tetrabutylammonium bromide. After stirring overnight, the chloroform layer was separated and the remaining aqueous layer was further extracted with chloroform. The combined chloroform layers were washed with water, dried and concentrated to give an orange oil. Chromatography using a mixture of ether and hexane (2:1) gave (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (0.92 g, 89% yield) as a pale yellow oil; 1H NMR: delta 2.52(3H,s), 3.59(3H,s), 3.73(3H,s), 6.55(1H,s), 7.17(1H,d), 7.20-7.55(3H,m), 7.45(1H,s), 8.57(1H,s) ppm.

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, 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; Clough, John Martin; Godfrey, Christopher Richard Ayles; Streeting, Ian Thomas; Cheetham, Rex; de Fraine, Paul John; Bartholomew, David; Eshelby, James John; US2003/60626; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1316216-05-3, Ethyl 2-(diphenylamino)pyrimidine-5-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, Application In Synthesis of Ethyl 2-(diphenylamino)pyrimidine-5-carboxylate, blongs to pyrimidines compound. Application In Synthesis of Ethyl 2-(diphenylamino)pyrimidine-5-carboxylate

0128] 2N NaOH (200 mL) was added to a solution of intermediate 3 (3.0 g, 9.4 mmol) in EtOH (200 mL). The mixture was stirred at 60C for 30 min. After evaporation of the solvent, the solution was neutralized with 2N HCl to give a white precipitate. The suspension was extracted with EtOAc (2 x 200 mL) and the organic layer was separated, washed with water (2 x 100 mL), brine (2 x 100 mL) and dried over Na2SO4. Removal of solvent gave a brown solid (2.5 g, 92%).

The synthetic route of 1316216-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; Golonzhka, Olga; Jarpe, Matthew B.; (30 pag.)US2017/114023; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

PREPARATION 17 5-(2-Ethoxy-5-nitrophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Concentrated nitric acid (0.5 ml) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (2.0 g, 0.0064 mol) in concentrated sulphuric acid (10 ml) at 0 C., an the resulting orange solution was stirred at room temperature for 18 hours. The reaction solution was then added dropwise to stirred ice and water (200 g) and the solid precipitate collected by filtration. This solid was then dissolved in dichloromethane (50 ml) and the solution washed successively with brine (2*30 ml) and water (30 ml), dried (Na2 SO4) and evaporated under vacuum to give a yellow solid. Crystallisation from acetronitrile gave the title compound as yellow needles (1.40 g, 61%), m.p. 214-216 C. Found: C,57.36; H,5.21; N,19.49. C17 H19 N5 O4 requires C,57.13; H,5.36; N,19.60%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Pfizer Inc.; US5272147; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8, 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate In a sealed tube, the mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.0 g, 2.9 mmol), ethynylcyclopropane (482 mg, 7.3 mmol), tetrakis(triphenyl-phosphine)palladium (335 mg, 0.29 mmol) and copper(I) iodide (28 mg, 0.15 mmol) in diethylamine (10 mL) and dimethyl sulfoxide (10 mL) was stirred at 100 C. for 3 hours under nitrogen atmosphere. The mixture was then diluted with ethyl acetate (100 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate=15:1 to afford tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate (930 mg, 98%) as a yellow solid. MS (ES+) C18H24N4O2 requires: 328, found: 329 [M+H]+.

According to the analysis of related databases, 374930-88-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia