Acetic Acid → 6-Benzyloxypurine

Participants

Reaction Conditions

Reaction Steps

Sodium (2.5 g, 109 mmol) was added to distilled benzyl alcohol (45 ml) under nitrogen. 6-Chloropurine (1.0 g, 6.47 mmol) was dissolved in distilled benzyl alcohol (73 ml) and the above solution (27 ml, 64.7 mmol) was added. The reaction was stirred at 100° C. under nitrogen for 5 days. After cooling to room temperature and neutralisation using glacial acetic acid, the solvent was removed in vacuo. Water (70 ml) was added and the product was extracted into ethyl acetate (3×30 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed. After further drying in vacuo, the product was recrystallised from acetone to yield the title compound as a white crystalline solid (0.39 g, 28%), m.p. 173-175° C.; (Found: C, 63.14; H, 4.29; N, 24.80. Calc. for C12H10N4O: C, 63.71; H, 4.46; N, 24.76%); δH (200 MHz, d6-DMSO) 8.480 (1H, s, C(2)H or C(8)H), 8.307 (1H, s, C(2)H or C(8)H), 7.522-7.301 (5H, m, Ph), 5.592 (2H, s, OCH2); m/z 226 (M+, 36%), 197 (8), 120 (35), 91 (Bn+, 100%), 81 (9), 65 (24), 57 (23), 43 (16), 32 (8).

Provenance & Evidence