Methanol → 2-Fluoroadenosine

Participants

Reaction Steps

2-Fluoro-2',3',5'-tri-O-acetyladenosine (0.41 g, 10 mmol) was dissolved in a mixture of 1,4-dioxane (7 mL) and water (2 mL) and the solution was cooled in an ice-water bath. 2.5 M NaOH (1.40 mL, 3.5 mmol) was added dropwise with vigorous stirring over a 2 min. period. The resulting bright yellow solution was stirred at 0° C. and monitored by TLC (9:1 Chloroform:methanol). After 2 hours, most of the yellow color had faded and TLC showed no acetylated intermediates remaining. The homogeneous reaction mixture was poured directly onto a column of AG 50-X4 (H+, 100-200 mesh, 10 mL bed volume) ion exchange resin and the column was eluted with several column volumes of 1:1 methanol:water. 2-Fluoroadenosine began to elute immediately, and all fractions which contained 2-fluoroadenosine were concentrated under vacuum to obtain a white partially crystalline solid which was dried overnight at 60° C. under vacuum: 0.20 g (70% yield), mp 220°-227° C. (d). This material was consistent by TLC, IR and UV with an authentic sample of 2-fluoroadenosine.

Provenance & Evidence