Реакция #168899

Уравнение реакции

N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

acrylic acid

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride salt

triethylamine

4-pyrrolidinopyridine

→

desired product

Выход 33.0%

N-(3-(4-(phenylthio)pyrimidin-2-ylamino)phenyl)acrylamide

Выход 33.0%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Промывкаwashed with water, 2.0 Maqueous sodium carbonate solution
2. 2
   Сушкаdried (Na2SO4)
3. 3
   ДругоеAfter removal of the solvent in vacuo
4. 4
   Другоеchromatographed on silica gel

Методика

To a stirred solution of N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine (80 mg, 0.27 mmol) and acrylic acid (37 μL, 0.54 mmol) in anhydrous dichloromethane (2 mL), was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride salt (78 mg, 0.41 mmol), triethylamine (114 μL, 0.82 mmol) and 4-pyrrolidinopyridine (5 mg). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 16 hours. It was diluted with dichloromethane (20 mL), washed with water, 2.0 Maqueous sodium carbonate solution, and dried (Na2SO4). After removal of the solvent in vacuo, the residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (50:50→100:0) as eluant to give the desired product (31 mg, 33%).

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