tert-Butylacrylamide → HCID 59975286, compound

Participants

Reaction Steps

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (250 mg, 0.48 mmol) was dissolved in stirred methanol (10 ml) and N-(tert-butyl)acrylamide (62 mg, 0.48 mmol) added. The reaction mixture was stirred for 24 hr at room temperature and then heated at reflux for 120 hr, at which time all solvent had evaporated. The residual reaction mixture was dissolved in dichloromethane and the solvent removed under reduced pressure, this procedure was repeated twice more and then the product purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:4:0.2) increasing in polarity to (93:7:0.3) to give the title compound (143 mg) as a foam. MS: 618 (MH+).

Provenance & Evidence