Formic Acid → HCID 135480760, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine (100 mg, 0.39 mmol) was dissolved in 80% formic acid solution and stirred at 100° C. for 2.5 hours. The reaction was evaporated to dryness under reduced pressure and the residue treated with methanol (5 ml) and 0.88 ammonia solution (3 ml). After stirring the reaction at 60° C. for 2 hours, the solvents were evaporated under reduced pressure and the residue recrystallised from water yielding the title compound (35 mg, 38%), m.p. 252°-3° C. Uv: λmax (H2O) 252 (ε12,600) nm; IR: υmax (KBr) 3330, 1690, 1640, 1605, 1540, 1475 cm-1 ; 1H NMR: δH [(CD3)2SO] 3.39 (2H, m, CH2OH), 3.72 (1H, m, CHOH), 4.10 (1H, dd, J=10.7, 7.6 Hz, 7.6 Hz, CH2ON), 4.33 (1H, dd, J=10.5, 3.3 Hz, CH2ON), 4.70 (1H, t, J= 5.7 Hz, OH), 5.15 (1H, d, J=5.2 Hz, OH), 6.62 (2H, br.s, NH2), 7.90 (1H, s, H-8), 10.58 (1H, br.s, NH); m/z 241 (M+, 3%), 210 (2), 167 (27), 151 (100), 109 (20), 61 (47). Found: C, 38.85; H, 4.66; N, 29.14%, M+ 241.0813. C8H11N5O4 requires C, 39.84; H, 4.60; N, 29.03%, M+ 241.0811.

Provenance & Evidence