Methanol → 2-Fluoroadenosine

Participants

Reaction Steps

2-Fluoro-2',3',5'-tri-O-acetyladenosine (0.41 9, 1.0 mmol, lt. yellow solid) was dissolved in a mixture of 1,4-dioxane (5 mL) and water (1 mL). The solution was stirred at ambient temperature and solid LiOH.circle-solid.H2O (1.40 mL, 3.5 mmol) was added in one portion. The progress of the reaction was monitored by TLC (9:1 Chloroform:methanol). After 2 hours, most of the suspended solid had dissolved and TLC showed no acetylated intermediates remaining. The cloudy 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: 0.18 g (63% yield), mp 227°-230° C. (d). This material was consistent by TLC, IR and UV with an authentic sample of 2-fluoroadenosine.

Provenance & Evidence