Ammonia → HCID 59875471, compound

Participants

Reaction Steps

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]tetrahydro-3-furanyl acetate (1.0 g, 1.91 mmol) (Preparation 11) in ethanol (40 ml) saturated with ammonia gas was 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 18 hours. TLC analysis showed that some starting material still remained and therefore further 5% w/w palladium on charcoal (0.25 g) and ethanol (20 ml) saturated with ammonia were added and the mixture was again pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 18 hours. The mixture was filtered through a pad of Arbocel (trade mark) and the filtrate was evaporated under reduced pressure. The residue was azeotroped from dichloromethane, then purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) to afford the title compound as a white solid (340 mg).

Provenance & Evidence