1-Bromo-2-Chloroethane → 4-Chloro-7-(2-bromoethoxy)-6-methoxyquinazoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-methoxyquinazolin-7-ol (5.0 g, 24 mmol), potassium carbonate (9.94 g, 72 mmol) and 1-bromo-2-chloroethane (7.98 ml, 96 mmol) in dimethyl acetamide (50 ml) was heated at 90° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and then filtered. The filtrate was purified directly by silica gel chromatography eluting with a 20 to 80% mixture of ethyl acetate in iso-hexane. The obtained product was triturated with diethyl ether to give a 3:1 mixture of 4-chloro-7-(2-chloroethoxy)-6-methoxyquinazoline: 4-chloro-7-(2-bromoethoxy)-6-methoxyquinazoline (4.77 g, 73% yield) as a white solid:

Provenance & Evidence