Benzyl Bromide → 7-Benzyl-3-phenylxanthine

Participants

Reaction Conditions

Reaction Steps

A solution of 0.53 g (13.2 mmol) of sodium hydroxide in 5.3 ml of water was added to a suspension of 3.0 g (13.2 mmol) of 3-phenylxanthine in 18 ml of methanol and the mixture was stirred at 70° C. for 1 hour. It was then treated dropwise with 1.56 ml (13.2 mmol) of benzyl bromide and stirred at 70° C. for 7 hours, the precipitate was filtered off with suction after cooling, washed with water and dissolved in 50 ml of 1 N sodium hydroxide solution, insoluble matter was filtered off and the solution was adjusted to pH 8-9 using 4 N hydrochloric acid. The resulting precipitate was filtered off with suction, washed with water and purified by flash chromatography on a silica gel column, dichloromethane/methanol (79/1).

Provenance & Evidence