Hydrochloric Acid → HCID 13869774, compound

Participants

Reaction Steps

To a suspension of 2-amino-6-chloro-9-(2-[2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.31 g, 1.0 mmol) in ethanol (1.5 ml) was added sodium ethoxide (1M in ethanol, 1.5 ml) and the mixture was stirred at 60° for 1 hour. The resulting solution was allowed to cool, hydrochloric acid (5M, 0.3 ml) and water (0.7 ml) were added and the solution was stirred for 1 hour at room temperature. The solution was neutralised by addition of aqueous sodium bicarbonate and the solvent was removed. The residue was extracted with chloroform-ethanol (2:1), the solution was filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chlorororm-methanol (6:1) to afford 2-amino-6-ethoxy-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (0.24 g, 85%), m.p. 150-152° C.; λmax (H2O) 213 (24,3000), 249 (7,360), and 280 (9,270) nm; νmax (KBr) 3330, 3210, 2900, 1650, 1610, 1580 cm−1; δH [(CD3)2SO] 1.3-1.6 (4H, m, 3′-H and CH3), 1.73 (2H, q, J 7 Hz, 2′-H), 3.2-3.6 (4H, AB part of ABX, 2×4′-H) 4.04 (2H, t, J 7 Hz, 1′-H), 4.3-4.55 (4H, m, 2H D2O exchangeable, 2×OH; D2O exchange leaves 2H, q, J 7 Hz, 6-OCH2), 6.30 (2H, s, D2O exchangeable, 2-NH2), and 7.84 (1H, s, 8-H); (Found: C, 50.91; H, 7.00; N, 24.89%; C12H19N5O3 requires C, 51.23; H, 6.81; N, 24.90%).

Provenance & Evidence