Ammonium formate → Famciclovir

Participants

Reaction Steps

A suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (0.36 g, 1.0 mmol) and 10% palladium-on-charcoal (30 mg) in methanol containing ammonium formate (400M, 10 ml) was heated under reflux for 30 minutes. The mixture was allowed to cool, filtered and the solvent removed. The residue was taken up in water and the solution extracted twice with chloroform. The organic layers were combined, dried (magnesium sulphate) and the solvent removed to afford 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.29 g, 90%). Recrystallisation from ethyl acetate-hexane gave white shiny plates (0.25g, 78%) m.p. 102°-104° C.; X@(MeOH) 222 (27,500), 244 (4,890), and 309 (7,16 0) nm; νmax (EBr) 3340, 3170, 1745, 1730, 1660, 1615 and 1580cm-1, &H (CDCl3) 1.90-2.05 (3H, m, 2'-H and 3'-H), 2.07 (6H, s, 2×CH3), 4.15 (4H, d, J 5.2 Hz, 2×4'-H) , 4.21 (2H, t, J 7.2Hz, 1'-H) , 5.16 (2H, br s, 2-NH2), 7.79 (1H, s, 8-H), and 8.70 (1H, s, 6-H); (Found: C, 52.10; H, 6.00; N, 21.49%. C14H19N5O4 requires C, 52.33; H, 5.96; N, 21.79%).

Provenance & Evidence