Pyridine → Famciclovir

Participants

Reaction Steps

To a suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (0.13 g, 0.55 mmol) in dry tetrahydrofuran (40 ml), stirred at room temperature under dry nitrogen were added pyridine (117 μl, 1.45 mmol) and 4-dimethylaminopyridine (5 mg, 41 μmol) followed by acetic anhydride (108 μl, 1.14 mmol). The mixture was stirred at room temperature for 5 h. giving a clear, colourless solution. T.1.c. [chloroform/methanol (9:1)] showed the major product to be the title compound, rf=0.40. Methanol (5 ml) was added, the mixture stirred for 5 mins. then evaporated to dryness. The residue was partitioned between water (5 ml) and chloroform (10 ml). The aqueous portion was extracted with chloroform (4×10 ml) then the combined organic portions dried over magnesium sulphate, filtered and evaporated to leave a pale yellow glassy material which was column chromatographed on silica (20 g) [eluant=chloroform/methanol (19:1)] to give the title compound (0.16 g, 91%) as a colourless viscous oil, which was crystallised from n-butanol (0.6 ml) to give colourless crystals (118 mg., 67%), m.p. 102° C.

Provenance & Evidence