Formic Acid → 6H-Purin-6-one, 2-amino-9-(4-(formyloxy)-3-((formyloxy)methyl)butyl)-1,9-dihydro-

Participants

Reaction Steps

A mixture of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (0.23 g, 0.9 mmol), dicyclohexylcarbodiimide (0.92 g, 4.5 mmol), formic acid (0.17 ml, 4.5 mmol), 4-dimethylaminopyridine (20 mg) and N,N-dimethylformamide (5 ml) was stirred for 40 minutes at room temperature and then quenched by addition of methanol (1 ml). The solution was filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (7:1, 4:1) to afford 9-(4-formyloxy-3-formyloxymethylbut-1-yl)guanine which was crystallised from methanol (0.12 g, 43%), m.p. 195-198° C.; νmax (KBr) 1720, 1680, 1630, 1600, and 1570 cm−1; δH [(CD3)2SO] 1.83 (2H, q, J 7.1 Hz, 2′-H), 2.01 (1H, m 3′-H), 4.04 (2H, t, J 7.1 Hz, 1′-H), 4.13 (4H, d, J 5.5 Hz, 2×4′-H), 6.39 (2H, s, D2O exchangeable, 2-NH2), 7.70 (1H, s, 8-H), 8.23 (2H, s, 2×HCOO), and 10.52 (1H, s, D2O exchangeable, 1-H); (Found: C, 45.40; H, 4.68; N, 21.70%; C12H15N5O5 requires: C, 46.60; H, 4.89; N, 22.64%).

Provenance & Evidence