N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide → N-({6-{[2,2-Bis(4-chlorophenyl)ethyl]amino}-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]urea

Participants

Reaction Steps

(2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol (0.1 g, 0.18 mmol) (Preparation 63) was dissolved in a mixture of isopropanol (0.5 ml) and Genklene (Trade Mark) (5 ml). N-[2-(Diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (48 mg, 0.20 mmol) (Preparation 27) was added and the reaction mixture was heated under reflux for 2 hours. More N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (35 mg, 0.15 mmol) (Preparation 27) was then added and the reaction mixture was heated under reflux for a further 2 hours. The reaction mixture was then allowed to cool and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:2 by volume) to give the title compound (0.09 g) as a gum.

Provenance & Evidence