Water → Penciclovir

Participants

Reaction Steps

2-Amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)-ethyl]purine (0.59 g, 1.9 mmol) in hydrochloric acid (1.0 M, 4 ml) was stirred at 60°60 C. for 24 hours. The solution was diluted with water and neutralised with Amberlite IR 45 (OH- form). The mixture was filtered, the resin washed with water and the solvent evaporated under reduced pressure. The residue was recrystallised from water to afford 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (238 mg, 49%), m.p. 275°-277° C.; λmax (H2O) 253 (ε11,500) and 270 (shoulder, ε8,630) nm; νmax (KBr) 3420, 3140, 1690, 1645, and 1605 cm-1 ; δH [(CD3)2SO] 1.3-1.5 (3 H, m, CHCH2CH2), 3.42 (4 H, d, J 5 Hz, 2×CH 2 O), 3.99 (2 H, t, J 7 Hz, CH2N), 4.41 (2 H, br, D2O exchangeable, 2×OH), 6.44 (2 H, s, D2O exchangeable, 2-NH2), 7.71 (1 H, s, 8-H), and 10.55 (1 H, br, D2O exchangeable, 1-H); (M+ found 253.1176. C10H15N5O3 requires M+ 253.1175).

Provenance & Evidence