Boron tribromide → HCID 135921361, compound

Participants

Reaction Steps

Boron tribromide (0.454 mL of a 1 M solution in dichloromethane, 0.45 mmol) was added to a solution of (S)-tert-butyl 3-(2-(2-methoxy-5-methylphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.079 g, 0.23 mmol) in dichloromethane (2.3 mL). After 16 hours, the reaction was quenched by the addition of methanol (2 mL). Hydrochloric acid (1.5 mL of a 4 M solution in dioxane) was added and the mixture was heated at reflux for 6 hours. The solution was cooled, concentrated, and purified by SCX-2 Isolute column (2 g), eluting first with methanol and finally 1 M ammonia in methanol. Silica column chromatography (5% methanol in DCM) gave the title compound as a yellow solid (0.025 g, 35%).

Provenance & Evidence