Pentane → HCID 59975279, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloronicotinonitrile (78 mg, 0.56 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 (250 mg, 0.51 mmol) (example 1) and triethylamine (57 mg, 0.56 mmol) in N-methyl-2-pyrrolidinone (10 ml). The reaction mixture was heated at 120° C. for 24 hr. The reaction mixture was then partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed with brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a residue that was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5) to give material that was still impure and hence re-purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:methanol (90:10) to give a yellow oil which was treated with pentane to give the title compound (47 mg) as a solid. MS: 594 (MH+).

Provenance & Evidence