Ammonia → HCID 59875475, compound

Participants

Reaction Steps

A solution of 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(1-naphthylmethyl)amino]-9H-purine-2-carbonitrile (0.75 g, 1.74 mmol) (Preparation 14) in ethanol (30 ml) was saturated with ammonia gas, treated with 5% w/w palladium on charcoal (0.50 g), pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 42 hours. TLC analysis indicated that some starting material still remained and therefore further 5% w/w palladium on charcoal (0.30 g) and ethanol (10 ml) saturated with ammonia gas were added. The mixture was re-pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 24 hours. The mixture was filtered through a pad of Arbocel (trade mark) and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (85:15:0.75 by volume) to afford the title compound (0.18 g).

Provenance & Evidence