Carbon Tetrachloride → 5-Amino-1-(5-chloro-5-deoxy-beta-d-ribofuranosyl)imidazole-4-carboxamide

Participants

Reaction Steps

AICA riboside (1.00 g), triphenylphosphine (3.05 g) and carbon tetrachloride (1.15 ml) were stirred in dimethyl formamide (38 ml) at room temperature for 3 hours. The solution was diluted with methanol (15 ml), then concentrated under reduced pressure. The resulting yellow tar was chromatographed on silica gel, eluting with 4:1 methylene chloride:methanol. The like fractions were combined and concentrated under reduced pressure to afford a purple foam. The presence of triphenylphosphine oxide, as determined by 1H NMR, necessitated a second chromotographic step as above. Yield was 0.43 g of a white foam.

Provenance & Evidence