1,2-Dichloroethane → Isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid (1.9 g, 11.8 mmol) in DMF (25 mL) is added HOBt (1.8 g, 13.4 mmol) followed by EDC (2.6 g, 13.4 mmol). The reaction mixture is stirred for 40 min until a clear solution is obtained and a solution of N-hydroxy-4-vinyl-benzamidine (2.09 g, 10.7 mmol) in DMF (20 mL) is added. After 2 h, EtOAc (320 mL) is added to the reaction mixture and the solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine, dried over MgSO4, filtered and evaporated to give a red oil. The oil is dissolved in dioxane (50 mL) and the solution is heated to 95° C. for 2 h. The reaction mixture is evaporated and purification by CC on silica gel affords the title compound as a yellow oil (2.79 g); LC-MS: tR=1.12; [M+H]+=321.95.

Provenance & Evidence