Water → 6,7-Dimethoxyquinazoline

Participants

Reaction Steps

Palladium (II) acetate (11 mg, 0.05 mmol) was added to a solution of 4-(4-iodophenoxy)-6,7-dimethoxyquinazoline (205 mg, 0.50 mmol), ethyl acrylate (50 mg, 0.50 mmol) and tri(o-tolyl)phosphine (30 mg, 0.10 mmol) in a mixture of triethylamine (3 ml) and acetonitrile (9 ml) and the reaction heated at reflux for 16 hours under an inert atmosphere. The reaction was cooled to ambient temperature, poured into water (30 ml), diluted with ethyl acetate (25 ml) and filtered through celite. The organic layer was separated, the aqueous was extracted with ethyl acetate (2×25 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/isohexane (1:1), yielded 4-(4-(2-carboethoxy)ethenyl)phenoxy)-6,7-dimethoxyquinazoline (130 mg, 68% yield) as a cream solid:

Provenance & Evidence