Cyclohexanemethanol → HCID 5329578, compound

Participants

Reaction Conditions

Reaction Steps

Sodium (0.4 g, 17.4 mmol) was added to stirred cyclohexylmethanol (10 ml) under nitrogen. The reaction was stirred at 100° C. until no sodium remained. 6-Chloropurine (500 mg, 3.24 mmol) was added, and the reaction was stirred under nitrogen at 100° C. for 5 days. After cooling to room temperature, the mixture was neutralised with glacal acetic acid and the solvent was removed in vacuo. Water (20 ml) was added and the product was extracted into dichloromethane (3×30 ml). The combined organic extracts were dried over MgSO4, and the volume of the solvent was doubled. After filtering hot and removal of the solvent, recrystallisation from ethyl acetate gave the title compound as a white crystalline solid (600 mg, 70%), m.p. 210-211° C.; (Found: C, 62.30; H, 6.93; N, 24.36. Calc. for C12H16N4O: C, 62.05; H, 6.94; N, 24.12%); νmax (cm−1) 3108, 3050,2930, 2849, 2801 (NH, C—H); δH (200 MHz, d6-DMSO) 8.479 (1H, s, C(2)H or C(8)H), 8.388 (1H, s, C(2)H or C(8)H), 4.348 (2H, d, J=6.2 Hz, OCH2), 1.854-1.692 (6H, m, cyclohexyl), 1.357-0.984 (5H, m, cyclohexyl); δC (50 MHz, d6-DMSO) 159.40, 155, 151.57, 142.88, 118, 71.41 (OCH2), 37.08, 29.40, 26.24, 25.47 (cyclohexyl); m/z 233 (MH+, 76%), 202 (33), 149 ([M—C6H11]+, 32%), 137 (100), 120 ([MH—C7H13O]+, 44%), 108 (30), 93 (27), 81 (65), 67 (62), 55 (88), 41 (89).

Provenance & Evidence