Trifluoroacetic acid → 9-(4-Hydroxy-3-hydroxymethyl-2-butenyl)guanine

Participants

Reaction Steps

A solution of 4-(2-amino-6-chloropurin-9-yl)-1-benzyloxy-2-benzyloxymethyl-2-butene (148 mg, 0.329 mmol), 1.8 ml of trifluoroacetic acid and 0.2 ml of water in a sealed ampoule was kept at 110° C. for 17 h. After cooling the mixture was diluted with 2 ml of water, heated to boiling for one minute, and evaporated to dryness in vacuum, dissolved in water and re-evaporated. Chromatography (silica gel, ethyl acetate+methanol+water 70+20+10 parts of volume) afforded 34 mg (41%) of 9-[4-hydroxy-3-(hydroxymethyl)-2-butenyl]guanine.

Provenance & Evidence