Benzenesulfonyl chloride → HCID 10231807, compound

Participants

Reaction Steps

A suspension of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol (0.16 g, 0.37 mmol) (Preparation 15) in dioxan (28 ml) was heated gently until a solution was achieved. The solution was cooled to room temperature and treated with triethylamine (0.12 g, 1.19 mmol) followed by addition of a solution of benzenesulphonyl chloride (0.060 g, 0.34 mmol) in dioxan (2 ml) over 10 minutes. The mixture was then stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the residue azeotroped with dichloromethane. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (92:8:0.4 by volume) to afford the title compound as a white solid (150 mg).

Provenance & Evidence