Methanol → HCID 178418823, compound

Participants

Reaction Steps

A solution of 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile (Preparation 15) (5.0 g, 14.7 mmol) and sodium methoxide (4.0 g, 74.1 mmol) in methanol (300 ml) was heated under reflux for 24 hours. Further sodium methoxide (2.0 g, 37 mmol) and methanol (100 ml) was then added and heating continued for a further 24 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The residue was dissolved in tetrahydrofuran (375 ml), 2 M aqueous hydrochloric acid solution (125 ml) added and the mixture stirred at room temperature for 24 hours. The tetrahydrofuran was removed under reduced pressure and the pH of the suspension adjusted to 7 with saturated aqueous sodium bicarbonate solution. Ethyl acetate (100 ml) was then added and the suspended white solid filtered off, washed with a little water then ethyl acetate and dried. Purification by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (90:10, by volume) gradually changing to dichloromethane:methanol (75:25, by volume) afforded the title compound as a white solid (1.25 g) (n.b. evaporation of the ethyl acetate filtrate provided 2.6 g of the starting material).

Provenance & Evidence