Aniline → 6-Acetoxy-7-methoxy-4-phenylamino-quinazoline

Participants

Reaction Conditions

Reaction Steps

6-Acetoxy-7-methoxy-quinazolin-4-one (RO0505111-000) was synthesized according to the literature procedure of Gibson, K. H. et al. Bioorganic & Medicinal Chemistry Letters, 1997, 7(21), 2723–2728. To a solution of 6-acetoxy-7-methoxy-quinazolin-4-one (RO0505111-000) (1.2 g, 5.13 mmol) in SOCl2 (30 mL) Aldrich) was added a few drops of DMF (0.1 mL). The reaction mixture was then heated with stirring at 100° C. for 3 hours. The solvents were evaporated and the residue was dried in vacuo. The residue was dissolved in 2-propanol (30 mL), then aniline (0.47 mL, 5.13 mmol) (Aldrich) was added. The reaction mixture was heated at 110° C. for 3 hours, then cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give 6-acetoxy-7-methoxy-4-phenylamino-quinazoline as a white solid. (Yield 1.0 g, 63%).

Provenance & Evidence