Ammonia → 2-{[(6-Hydroxy-2-imino-2,3-dihydro-9H-purin-9-yl)oxy]methyl}propane-1,3-diol

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Reaction Conditions

Reaction Steps

A mixture of 9-(3-benzyloxy-2-benzyloxymethylprop-1-oxy)-2-formamido-6-chloropurine (2.5 g, 5.2 mmol) and 80% formic acid (100 ml) was stirred at 100° C. for 1 hour, cooled and 10% palladium on charcoal (2.0 g) added. The mixture was then stirred under an atmosphere of hydrogen for 45 minutes. The catalyst was removed and the solution evaporated under reduced pressure. The residue obtained was heated in water (100 ml) until boiling commenced. Concentrated aqueous ammonia (4 ml) was added and the solution was then heated for a further 15 minutes, cooled and evaporated under reduced pressure. Recrystallisation from water (charcoal) afforded 9-(3-hydroxy-2-hydroxymethylprop-1-oxy)guanine (430 mg, 32%). IR: υmax (KBr) 3380, 3183, 1679, 1637, 1605, 1541, 1479, 1395 cm-1. 1H NMR: δH [(CD3)2SO] 1.94 (1H, m, CH), 3.53 (4H, m, 2×CH2OH), 4.26 (2H, d, J=6.3 Hz), 4.57 (2H, t, J=5.2 Hz, D2O exchangeable, 2×OH), 6.58 (2H, br.s, NH2), 7.92 (1H, s, H-8), 10.64 (1H, br.s, D2O exchangeable, H-1). Found: C, 42.08; H, 5.15; N, 27.41%. C9H13N5O4 requires: C, 42.34; H, 5.14; N, 27.44%.

Provenance & Evidence