Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methylthioethoxy)quinazoline

Participants

Reaction Steps

1M Ethereal hydrogen chloride (3.1 ml, 3.1 mmol) was added to 4-chloro-6-methoxy-7-(2-methylthioethoxy)quinazoline (0.8 g, 2.8 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (0.44 g, 3.12 mmol), (prepared as described for the starting material in Example 8), in isopropanol (25 ml). The mixture was heated at reflux for 2 hours, then allowed to cool. The resulting suspension was diluted with acetone and the precipitate collected by filtration and purified by column chromatography eluting with methylene chloride/methanol/ammonia (100/8/1) to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methylthioethoxy)quinazoline (580 mg, 52%).

Provenance & Evidence