Allyl bromide → (6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol (0.70 g, 2.18 mmol) (from Example 18, Step B, supra) in acetone (140 mL) was added K2CO3 (0.61 g, 10.9 mmol) and allyl bromide (0.94 mL, 10.9 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2C2/Et3N (1:1:0.02) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine as an off white solid. (Yield 0.64 g, 82%).

Provenance & Evidence