2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 11613488, compound

Participants

Reaction Steps

A solution of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloropurine (2.41 g, 5.4 mmol) and 2-butylimidazole (6.68 g, 54 mmol) in CH3CN (60 mL) was stirred at 65° C. under N2 for 32 h (reaction complete, TLC). Volatiles were evaporated in vacuo, and the residue was chromatographed (MeOH/CH2Cl2, 1:90) to give crude 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(2-butylimidazol-1-yl)-2-chloropurine (3.33 g, contaminated with 2-butylimidazole): 1H NMR (500 MHz, CDCl3) δ 8.56 (s, 1H), 8.24 (s, 1H), 7.10 (s, 1H), 6.26 (d, J=5.8 Hz, 1H), 5.83 (t, J=5.6 Hz, 1H), 5.61 (t, J=5.6 Hz, 1H), 4.43-4.51 (m, 3H), 3.31 (t, J=7.9 Hz, 2H), 2.18 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 1.81 (quint, J=7.7 Hz, 2H), 1.50 (sext, J=7.7 Hz, 2H), 0.98 (t, J=7.3 Hz, 3H); HRMS m/z 535.1702 (MH+[C23H28ClN6O7]=535.1708).

Provenance & Evidence