Ammonia → Deoxyuridine

Participants

Reaction Steps

For example, addition of excess acetyl bromide (3.2 eq) plus 30% HBr in acetic acid (1.2 eq) to uridine at 55°-60° C. gave the desired 3',5'-di-O-acetyl-2'-bromo-2'-deoxyuridine 2 (FIG. 1; X=O in uridine and uridine derivatives) in excellent yield (>95%). 3',4'-Di-O-acetyl-2'-bromo-2'-deoxyuridine 2 was then reduced to 3 by tributyltin hydride (provided either as the premade compound or prepared by in situ generation through the reaction of tributyltin chloride with sodium borohydride) in absolute ethanol in excellent yield (>95%). 2',3'-Di-O-acetyl-2'-deoxyuridine was treated with methanolic ammonia to obtain an excellent yield of 2'-deoxyuridine. The overall yield of this process was 72-76% without chromatography.

Provenance & Evidence