Reacción #168899

Ecuación de reacción

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

Rendimiento 33.0%

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

Rendimiento 33.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water, 2.0 Maqueous sodium carbonate solution
2. 2
   Secadodried (Na2SO4)
3. 3
   OtroAfter removal of the solvent in vacuo
4. 4
   Otrochromatographed on silica gel

Procedimiento

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%).

Fuente