Sodium Hydroxide → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-7-hydroxyquinazoline

Participants

Reaction Steps

1M Aqueous sodium hydroxide solution (2.1 ml, 2.1 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxyquinazoline hydrochloride (400 mg, 1.05 mmol), in methanol (10 ml) and the mixture stirred for 50 minutes at ambient temperature. The solvent was removed by evaporation, the residue dissolved in water and adjusted to pH7 with hydrochloric acid. The aqueous mixture was extracted with ethyl acetate, the extracts washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol 95/5 and 80/20. The purified solid was dissolved in methanol and saturated methanolic hydrogen chloride was added. The volatiles were removed by evaporation, the residue was triturated with pentane to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-hydroxyquinazoline (149 mg, 44%) as a yellow solid.

Provenance & Evidence