tert-Butyl (4-aminophenyl)carbamate → [4-(4-Dimethylamino-quinazolin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (0.5 g, 2.6 mmol) and (4-amino-phenyl)-carbamic acid tert-butyl ester (0.5 g, 2.6 mmol) in CH2Cl2 (2 mL) was heated by Smith Synthesizer at 130° C. for 20 min. The mixture was concentrated to give [4-(4-dimethylamino-quinazolin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester as a pale yellow solid (0.86 g, 87%). The reaction was repeated six times, and the total product combined was 8.5 g. To a solution of above product (8.5 g, 22.4 mmol) in MeOH (250 mL) was added 4 M HCl in dioxane (8.4 ml, 33.6 mmol) dropwise, and the mixture was stirred at ambient temperature for overnight. The mixture was concentrated to give N2-(4-amino-phenyl)-N4,N4-dimethyl-quinazoline-2,4-diamine hydrochloride as a pale pink solid (6.2 g, 87.5%).

Provenance & Evidence