2-Propanesulfonyl chloride → HCID 9894877, compound

Participants

Reaction Steps

Isopropylsulphonyl chloride (120 mg, 0.84 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (408 mg, 0.8 mmol) (example 1) in 2,6-lutidine (10 ml). The mixture was stirred at room temperature for 24 hr followed by stirring at 50° C. for a further 5 days. A second portion of isopropylsulphonyl chloride (120 mg, 0.84 mmol) and lutidine (4 ml) were added and the reaction stirred at 50° C. for 24 hr. A third portion of isopropylsulphonyl chloride (120 mg, 0.84 mmol) was added and heating at 50° C. continued for a further 24 hr. At the end of this period the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous ammonia. The organic phase was separated and the solvent removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (98:2:0.1) increasing to dichloromethane:methanol:ammonia (96:4:0.2). This gave the title compound (118 mg) as an oil. MS: 597 (MH+).

Provenance & Evidence