Dimethylformamide → 6H-Purin-6-one, 9-(3-(acetyloxy)propoxy)-2-amino-1,9-dihydro-

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Reaction Conditions

Reaction Steps

A mixture of 9-(3-hydroxyprop-1-oxy)guanine (150 mg, 0.67 mmol), 4-dimethylaminopyridine (15.6 mg, 0.13 mmol), acetic anhydride (0.25 ml, 2.65 mmol) and N,N-dimethylformamide (5 ml) was stirred at 20° C. for 3 hours and then ethanol was added. After a further 15 minutes the solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (eluted with chloroform-ethanol, 4:1), yielding the title compound (120 mg, 67%). Recrystallisation from methanol-water gave 9-(3-acetoxy-prop-1-oxy)guanine (82 mg, 46%). IR: υmax (KBr) 3330, 3168, 1736, 1696, 1648, 1602, 1589, 1391 cm-1. 1H NMR: δH [(CD3)2SO] 1.98 (2H, quintet, J=6.3, 6.6 Hz, CH2CH2CH2), 2.02 (3H, s, ##STR14## 4.17 (2H, t, J=6.6 Hz, CH2ON), 4.32 (2H, t, J=6.3 Hz, ##STR15## 6.60 (2H, br.s, D2O exchangeable NH2), 7.94 (1H, s, H-8), 10.69 (1H, br.s, D2O exchangeable, H-1). Found: C, 44.99; H, 4.93; N, 26.20% M+ 267.0964 C10H13N5O4 requires C, 44.93; H, 4.91; N, 26.21% M+ 267.0968.

Provenance & Evidence