N-(2-Aminoethyl)piperidine → HCID 178465183, compound

Participants

Reaction Steps

Dimethyl cyanodithioimidocarbonate (77 mg, 0.48 mmol) was added to a solution of (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (250 mg, 0.48 mmol) (Preparation 11) in ethanol 10 ml). The reaction mixture was stirred for 3 hours at room temperature and then 2-aminoethylpiperidine (88 μl, 0.68 mmol) was added. The reaction mixture was heated under reflux for 2 hours, more 2-aminoethylpiperidine (0.17 ml, 1.2 mmol) was added and then the reaction mixture was heated under reflux for a further 4 hours. The reaction was cooled and evaporated to dryness and the residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume) to give the title compound (64 mg) a foam.

Provenance & Evidence