Ammonia → HCID 53967906, compound

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A mixture of methyl 5-cyanomethyl-1-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylate (2.20 g, 6.03 mmol) and liquid ammonia (30 ml) was placed in a steel bomb (40 ml) and heated at 100° for 7 hr. The ammonia was allowed to evaporate and the residue was subjected to a vacuum overnight to remove the last traces. The residue was absorbed on silica gel (5 g) and placed on a column of silica gel (60 g, packed in chloroform). Elution with chloroform-methanol (4:1) provided the pure product. Recrystallization from methanol provided colorless cubes (1.42 g, 88%); mp 173°-174° after drying at 100° for 3 hr; [α]D25 -47.8 C=1, H2O); uv λmaxpH 1 218 nm (ε 10,000), λmaxpH 7 233 nm (ε 10,200), λmaxpH 11 234 nm (ε 9,730); pmr (DMSO-d6): δ 1.35 (d,3,CH3), 5.66 (d,1,H1'), J = 5 Hz, 7.45 (d,2,NH2), 8.02 (s,1,C2H).

Provenance & Evidence