Allylamine → 3-Allyl-7-bromoquinazoline-2,4(1H,3H)-dione

Participants

Reaction Steps

BOP (8.47 g, 19.16 mmol) was added to a solution of 4-bromo-2-[(ethoxycarbonyl)amino]benzoic acid (4.6 g, 15.97 mmol), N-methylmorpholine (3.51 ml, 31.9 mmol) and allylamine (1.434 ml, 19.16 mmol) in DMF (50 ml) at room temperature. The mixture was allowed to stir at room temperature for 4 hrs. DBU (24.07 ml, 160 mmol) was added to the reaction and the temperature was raised to 60° C. The mixture let was allowed to stir at 60° C. for 1 hr. The mixture was quenched into 0.5 N HCL (200 mL), and the pH was adjusted to 1.5 with 3N HCL. Thick white solids were observed. The reaction was diluted to ˜400 mL with water let stir 10 min and solids filtered. The solids were washed with 0.5 N HCL (50 mL) and then slurry washed with water and sucked dry overnight to give the title compound (4.5 gm, 100%) as a solid. LCMS (ES+) m/z 280.87 (M+H)+.

Provenance & Evidence