Sodium ethoxide → HCID 22160550, compound

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Reaction Steps

A solution of 9-(3-benzyloxyprop-1-oxy)-6-chloro-2-formamidopurine (500 mg, 1.38 mmol) in 0.4M sodium ethoxide in ethanol (10 ml) was heated at 80° C. for 2.5 hours. The mixture was then cooled and evaporated under reduced pressure. The residue was dissolved in water (20 ml) and the solution was brought to pH 7 with dilute hydrochloric acid. The aqueous solution was extracted with chloroform (2×20 ml) and the combined extracts were washed with water (10 ml), dried (magnesium sulphate) and evaporated under reduced pressure. Column chromatography on silica gel (eluted with chloroform-ethanol, 50:1) yielded the title compound (390 mg, 8%). IR: υmax (KBr) 3353, 3217, 1652, 1611, 1579, 1506, 1461, 1445, 1407 cm-1. 1H NMR: δH [(CD3)2SO] 1.35 (3H, t, J=7.2 Hz, CH3CH2O), 1.95 (2H, quintet, J=6.3, 6.6 Hz, CH2CH2CH2), 3.60 (2H, t, 6.3 Hz), 4.37 (2H, t, J=6.6 Hz, CH2ON), 4.42 (2H, quartet, J=7.2 Hz, CH3CH2O), 4.48 (2H, s, CH2Ph), 6.55 (2H, br.s, D2O exchangeable, NH2), 7.33 (5H, m, Ph), 8.07 (1H, s, H-8).

Provenance & Evidence