Dimethylformamide → HCID 21717189, compound

Participants

Reaction Steps

A solution of oxindole (1.2 g, 9 mmol) in THF (10 ml) was added dropwise to a suspension of sodium hydride (360 mg of a 60% suspension in paraffin oil, 9 mmol) in THF (15 ml) over 15 minutes under nitrogen. The resulting white suspension was stirred for 15 minutes at ambient temperature and a solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline (900 mg, 3 mmol) in THF (10 ml) was added followed by DMF (5 ml). The resulting reddish solution was stirred for 30 minutes at ambient temperature followed by 1 hour at 65° C. The mixture was concentrated to half its volume by evaporation and was partitioned between ethyl acetate and water. The aqueous layer was separated, adjusted to pH7 with 2M hydrochloric acid and the resulting precipitate was collected by filtration, washed with water, followed by ethyl acetate and ether and dried under vacuum to give 7-benzyloxy-6-methoxy4-(oxindol-3-yl)quinazoline (1 g, 83%) as a yellow solid.

Provenance & Evidence