Dimethylformamide → HCID 68882807, compound

Participants

Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (1.4 ml) in tetrahydrofuran (1.0M, 1.4 mmol) was added dropwise to an ice-cold solution of 5-bromo-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.208 g, 0.70 mmol) and 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (0.201 g, 0.70 mmol) in dimethylformamide (10 ml). The mixture was allowed to warm to room temperature over 2 hours and then stirred at room temperature overnight. A saturated solution of ammonium chloride (25 ml) was added and the mixture was then extracted with ethyl acetate (25 ml). The organic layer was separated, washed with a saturated solution of sodium chloride (25 ml), dried over magnesium sulfate and evaporated under reduced pressure to leave a brown oil. Flash chromatography on silica eluting with a 1:1 to 3:1 mixture of ethyl acetate and iso-hexane gave the product as a brown gum (0.245 g).

Provenance & Evidence