Chlorosuccinimide → 1-(4-Hydroxy-3-(hydroxymethyl)-1-butyl)-5-(1-azido-2-chloroethyl)uracil

Participants

Reaction Conditions

Reaction Steps

N-Chlorosuccinimide (50 mg, 0.37 mmol) was added slowly with stirring to a precooled (−5° C.) suspension, prepared by mixing a solution of 20 (75 mg, 0.31 mmol) in 1,2-dimethoxyethane (25 ml) with a solution of sodium azide (81 mg, 1.24 mmol) in water (0.23 ml). The reaction mixture was allowed to proceed for 2 h at 0° C. with stirring and the solvent was removed in vacuo. The resulting residue was purified by silica gel column chromatography using chloroform:methanol (90:10, v/v) as eluent to afford 21b (46 mg, 47%) as a viscous oil.

Provenance & Evidence