Triethylamine → 4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-methoxyacetamidoquinazoline

Participants

Reaction Steps

Methoxyacetyl chloride (119 mg, 1.1 mmol) followed by triethylamine (232 mg, 2.3 mmol) were added to a suspension of 7-amino-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride (415 mg, 1.1 mmol) in methylene chloride (10 ml) and the mixture stirred for 1 hour. The solvent was removed by evaporation and the residue partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The resulting solid was purified by column chromatography eluting with methylene chloride/acetonitrile 50/50 followed by methylene chloride/acetonitrile/methanol 50/45/5 to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-methoxyacetamidoquinazoline (250 mg, 60%) as a yellow solid.

Provenance & Evidence