2-Phenylethanol → HCID 18365127, compound

Participants

Reaction Conditions

Reaction Steps

2-Phenylethanol (13 ml) was stirred under nitrogen and sodium (0.75 g, 32.36 mmol) was added. The reaction was heated to 60° C. When no sodium remained, anhydrous THF (18 ml) and 6-chloropurine (1.0 g, 6.47 mmol) were added. After refluxing under nitrogen for 5 h, the reaction mixture was allowed cool to room temperature and neutralised with glacial acetic acid. The THF was removed and the remaining alcohol was removed in vacuo. The product was recrystallised from ethanol and isolated as a white crystalline solid (962 mg, 62%), m.p. 209-210° C.; (Found: C, 64.57; H, 5.12; N, 23.54. Calc. for C13H12N4O: C, 64.99; H, 5.03; N, 23.34%); νmax (cm−1) 3135,3063, 3031, 2948, 2897, 2797, 2672, 2583 (NH, C—H); δH (200 MHz, d6-DMSO) 8.483 (1H, s, C(2)H or C(8)H), 8.365 (1H, s, C(2)H or C(8)H), 7.366-7.194 (5H, m, Ph), 4.741 (2H, t, J=7.0 Hz, OCH2), 3.134 (2H, t, J=7.0 Hz, CH2Ph); m/z 240 (M+, 11%), 149 ([M—Bn]+, 11%), 136 ([M—CH2CH2Ph]+, 87%), 119 ([M—OCH2CH2Ph]+, 40%), 104 ([CH2CH2Ph]+, 100%), 91 (BN+, 37%), 77 (Ph+, 55%), 69 (48), 65 (15), 51 (26).

Provenance & Evidence