Water → 6,7-Dimethoxyquinazoline

Participants

Reaction Steps

Palladium (II) acetate (303 mg, 1.35 mmol) was added to a solution of 4-(4-iodoanilino)-6,7-dimethoxyquinazoline (6.00 g, 13.5 mmol), ethyl acrylate (1.35 g, 13. 5 mmol) and tri(o-tolyl)phosphine (821 mg, 2.70 mmol) in a mixture of triethylamine (60 ml) and acetonitrile (200 ml) and the reaction heated at reflux for 20 hours under an inert atmosphere. The reaction was cooled to ambient temperature, poured into water (600 ml), diluted with ethyl acetate (200 ml) and filtered through celite. The organic layer was separated, the aqueous was extracted with ethyl acetate (2×200 ml) and the combined organic layers were dried over magnesium sulphate before solvent evaporation in vacuo. Purification by flash chromatography on silica gel, eluting with ethyl acetate, yielded 4-(4-(2-carboethoxy)ethenyl)anilino)-6,7-dimethoxyquinazoline (4.36 g, 85% yield) as a yellow solid:

Provenance & Evidence