Potassium Carbonate → 5-Fluoro-1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-fluorocytosine (0.80 g, 6.20 mmol), anhydrous potassium carbonate (40 mg) and anhydrous dimethyl formamide (15 mL) is heated to 70° C. under a nitrogen atmosphere. Then rac-1,2-epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) is added to this mixture with stirring over a period of 1 hour. The resultant reaction mixture is stirred at 80°-90° C. (oil bath temperature) for 48 hours. The reaction mixture is cooled to room temperature and concentrated under reduced pressure (0.5 mm Hg) to afford the crude product as a cream solid. This crude material is purified by chromatography and dried in vacuo to give 0.6 g (22%) 5-fluoro-1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine (CPR 1152): Thin-layer Chromatography (TLC; 4×8 cm silica gel 60, 0.25 mm thickness): 8:2 (v/v) CHCl3 -CH3OH (Rf value=0.75); mp 118°-119° C.

Provenance & Evidence