Category: 5909-24-0

Related Products of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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.

In DCM (100 mL) were dissolved ethyl 4-chloro-2-(methylthio) pyrimidine-5-carboxylate (5.0 g, 21.55 mmol), 3-chloro-4-methoxybenzylamine (4.0 g, 23.4 mmol) and triethylamine (4.35 g, 43.1 mmol). The reaction mixture was stirred at ambient temperature for 10 h and washed with water. The organic phase was dried over magnesium sulfate and concentrated to give ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2 -(methylthio)pyrimidine-5-carboxylate as a solid (6.0 g, 76 % yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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 ethyl 4-chloro-2- (methylthio)pyrimidine-5-carboxylate (20.0 g, 86 mmol) in dichloromethane (400 mL) at -78 0C was added diisobutylaluminum hydride, 1.0 M in toluene (172 mL, 172 mmol). The reaction was allowed to warm to 0 0C over 2 h. To the reaction was added a 20% Rochelle’s (1600 mL) and diethyl ether (750 mL). The emulsion was stirred for 30 min. The organics were sequestered and the aqueous was extracted further with diethyl ether (2 x 500 mL). The combined organics were washed with water (500 mL), brine (500 mL), dried over MgSO4, and concentrated in vacuo and filtered through a plug of silica eluting with 1:1; ethyl acetate:CH2Cl2 to obtain compound 223 (9.6 g, 59% yield). 1H NMR (500 MHz, CDCl3) delta 8.55 (s, 1 H) 4.75 (d, J=5.87 Hz, 2 H) 2.58 (s, 3 H) 2.06 – 2.25 (m, J=5.14 Hz, 1 H) ppm.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); 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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H9ClN2O2S

In THF (150 mL) was suspended 3-chloro-4-methoxybenzylamine hydrochloride salt (16.0 g, 76.9 mmol). The suspension was cooled in an ice bath, and triethylamine (19.4 g, 192.3 mmol) was added dropwisely. The reaction mixture was stirred at ambient temperature for 15 min, then was added ethyl 4-chloro-2-thiomethyl-5-pyrimidine carboxylate (14.9 g, 64.1 mmol). The reaction mixture was stirred at ambient temperature overnight. TLC was used to monitor the reaction. After the completion of the reaction, the solvent was removed by rotary evaporation. Acetic ether (500 mL) and water (200 mL) were added. The organic phase was separated, washed with hydrochloric acid (1N), saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The solvent was removed by rotary evaporation to give oil. Methanol (100 mL) was added to precipitate a large amount of white solid. The mixture was filtrated and the solid was dried in vacuum to give ethyl 4-((3-chloro-4-methoxybenzyl)amine)-2-thiomethyl-5-pyrimidine carboxylate (21 g, 74.2 % yield).

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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.

After dissolving 50.0 g of 4-chloro-5-ethoxycarbonyl-2-methylthiopyrimidine and 59.9 ml of triethylamine into 430 ml of ethyl acetate, respectively, the mixture was cooled to 0 C, 44.7g of 3-chloro-4-methoxybenzylamine was added in portions, the reaction was carried out at 0-5 C for 30min and the reaction was continued at 20-30 C for 0.5-1h. The reaction was concentrated under reduced pressure, and then added ethyl acetate and citric acid solution 400ml each wash 2 times, the organic phase was washed with water and saturated brine each time, dried, filtered and concentrated under reduced pressure to give the crude 73.0g. Finally, with anhydrous ethanol at 55 ~ 60 C dissolved crude, stirring crystallization 12-18h, filtered and dried to give the product 42.3g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5909-24-0, its application will become more common.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Chen Yuhua; Lu Pingping; Mo Enqing; Zuo Lian; Lu Zhijun; Peng Guizi; Yuan Yongling; (14 pag.)CN104059025; (2017); B;,
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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate

To 600ml of methylene dichloride was added lOOg of ethyl 4-chloro-2-(methylsulfanyl) pyrimidine-5-carboxylate and 91.2g of 3-chloro-4-methoxybenzylamine. The reaction mixture was stirred and 500m1 of water, 48g of sodium carbonate and Ig of tetra-butylammonium bromide were added to it. The reaction mixture was then maintained overnight at 25-30C. After completion of reaction, methylene dichloride layer was separated, washed with water and evaporated to obtain 145g of ethyl 4-[(3-chloro-4-methoxybenzyl) amino]-2-(methyl sulfanyl) pyrimidine-5-carboxylate having 95% of HPLC purity.

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; WANBURY LTD.; NITIN SHARADCHANDRA PRADHAN; VIHAR RAGHUNATH TELANGE; SURYAKANT SHIVAJI POL; SHASHIKANT BALU PADWAL; NITN SHANKAR BONDRE; WO2015/177807; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5909-24-0, 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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

260 mL of N,N-diisopropylethylamine and 106 g of the hydrazine obtained in the above 1 were added to tetrahydrofuran (1.5 L) solution of 142 g of ethyl 4-chloro-2-(methylthio)pyridine-5-carboxylate, and stirred with heating under reflux for 18 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, and 500 mL of diethyl ether was added to the residue, and the precipitated solid was separated through filtration. The filtrate was evaporated under reduced pressure, the residue was cooled in an ice bath, 400 mL of trifluoroacetic acid was gradually added thereto, and stirred at room temperature for 1 hour and then at 70 C. for 1 hour. The reaction solution was evaporated under reduced pressure, 500 mL of ethanol was added thereto and cooled in an ice bath, and 1.0 L of 6 N sodium hydroxide solution was added thereto and stirred at room temperature for 15 minutes. Cooled in an ice bath, the reaction solution was made acidic with 400 mL of concentrated hydrochloric acid, and then evaporated under reduced pressure. The residue was partitioned in chloroform and water, and the chloroform layer was extracted, washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the formed yellow solid was taken out through filtration, washed with ethanol and diethyl ether, and dried to obtain 99.1 g of the entitled compound as a yellow solid.1H-NMR (400 MHz, DMSO-d6) ?: 8.66 (1.0H, brs), 5.83 (1.0H, ddt, J=17.1, 9.8, 5.4 Hz), 5.13 (1.0H, d, J=9.8 Hz), 5.06 (1.0H, d, J=17.1 Hz), 4.34 (2.0H, d, J=5.4 Hz), 2.51 (3.0H, s).ESI-MS Found: m/z[M+H]+ 223.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sagara, Takeshi; Otsuki, Sachie; Sunami, Satoshi; Sakamoto, Toshihiro; Niiyama, Kenji; Yamamoto, Fuyuki; Yoshizumi, Takashi; Furuyama, Hidetomo; Goto, Yasuhiro; Bamba, Makoto; Takahashi, Keiji; Hirai, Hiroshi; Nishibata, Toshihide; US2007/254892; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5909-24-0, Ethyl 4-chloro-2-(methylthio)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, 5909-24-0, blongs to pyrimidines compound. 5909-24-0

(3) 50 g of the compound of formula (5) was dissolved in 300 ml of tetrahydrofuran,Nitrogen protection,Add 400ml (1.5mol / L)Diisobutylaluminum hydride,Room temperature stirring,Reaction for 4 hours,Add 300ml saturated ammonium chloride dissolved in quenching,Further, 600 ml of ethyl acetate and 300 ml of potassium tartrate solution were added and stirring was continued for 1.5 hours,Dispensing,Concentrate the organic phase of the compound of formula (6)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5909-24-0, its application will become more common.

Reference:
Patent; East China Normal University; Hu Wenhao; Chang Huan; Xu Haiqun; Huang Haifeng; Ma Mingliang; (21 pag.)CN106749259; (2017); 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.5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C8H9ClN2O2S, molecular weight is 232.6873, as common compound, the synthetic route is as follows.5909-24-0

[4-C hlor o-2-(methylthio)pyrimidin-5-yl] methanol. 4-Chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (62 g, 260 mmol) was dissolved in anhydrous tetrahydrofuran (500 mL) in a 3-necked 5L round bottomed flask fitted with a mechanical stirrer, addition funnel, temperature probe and nitrogen inlet. The solution was cooled to 0C. Diisobutylaluminum hydride in tetrahydrofuran (1M solution, 800 mL) was added dropwise over a period of 2 hours. After the addition was complete, the reaction mixture was kept at 0C for 0.5 hours. The reaction was quenched at 0C by the slow addition of saturated aqueous sodium sulfate (265.3 mL, 530.7 mmol) keeping the internal reaction temperature below 10C. Ethyl acetate (900 mL) was added and the reaction slowly warmed to room temperature overnight. 6M HC1 was added till the reaction mixture was slightly acidic (pH 6). The reaction mixture was filtered thru a pad of Celite and the aluminum salts were washed with ethyl acetate (1L). The filtrate was poured into a separatory funnel and washed twice with water (600 mL) and finally with brine (600 mL). The organic layer was dried over sodium sulfate, filtered thru Celite and the solvent concentrated in vacuo to afford 39.2g (77% crude yield) of a dark yellow oil. The material was used as is for the next step. NMR (CDCI3) delta 8.56 (s, 1H), 4.76 (s, 2H), 2.59 (s, 3H); MS (ESI+) for C6H7C1N20S m/z 191.0 (M+H)+ .

Statistics shows that 5909-24-0 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; GASTON, Ricky, D.; GADWOOD, Robert, C.; WO2015/161287; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5909-24-0, Adding a certain compound to certain chemical reactions, such as: 5909-24-0, Ethyl 4-chloro-2-(methylthio)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, 5909-24-0, blongs to pyrimidines compound.

step 1: To ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (370.0 g, 1.59 mol) in DCM (7.4 L) at -78 C. was added diisobutylaluminum hydride (1.5 M in toluene, 2.1 L, 3.18 mol). The reaction mixture was allowed to warm to 0 C. over 2 h. To the reaction was added a 20% Rochelle’s salt solution (5.0 L). The emulsion was stirred for 30 min. The mixture was filtered through a bed of CELITE. The organic layer was separated and the aqueous layer extracted with EtOAc (1.0 L¡Á3). The combined organic layers were dried ((Na2SO4)), filtered, and concentrated in vacuo to give the crude product (4-chloro-2-(methylthio)pyrimidin-5-yl)methanol as a solid. The crude product was purified by SiO2 chromatography eluting with DCM/EtOAc (1:1) to afford the pure product (4-chloro-2-(methylthio)pyrimidin-5-yl)methanol (133.0 g, 44.0%) as a solid. 1H NMR (400 MHz, CDCl3) delta 8.55 (s, 1H), 4.74 (s, 2H), 2.58 (s, 3H); MS: 191 [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,5909-24-0, its application will become more common.

Reference:
Patent; GENENTECH, INC.; Rudolph, Joachim; Gazzard, Lewis J.; Crawford, James J.; Ndubaku, Chudi; Drobnick, Joy; Lee, Wendy; US2015/31674; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5909-24-0, 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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

3-chloro-4-methoxybenzylamine (45.6 g, 0.27 mol) was dissolved in 180 mL of acetone, then triethylamine (40.4 g, 0.4 mol) was added.4-chloro-2-methylthiopyrimidine-5-carboxylic acid ethyl ester obtained in the step S2(53.3 g, 0.24 mol) dissolved in 250 mL of acetone and slowly dropped into the reaction solution.And reacted at room temperature for 3 h, and poured the reaction solution into the ice water mixture.Extracted with ethyl acetate,The combined organic phases were washed with 10% aqueous citric acid (250 mL x 3).Dry the organic layer with anhydrous sodium sulfate.Evaporate the solvent under reduced pressure.Dry in vacuo to a white solid (86.0 g, 87.0%).

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 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Suzhou Zhonglian Chemical Pharmaceutical Co., Ltd.; Yang Huxing; Huang Junhao; Luo Xinzu; (12 pag.)CN108707141; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia