Isopropylamine → 5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine

Participants

Reaction Steps

Following General Procedure V, isopropylamine (Aldrich, 3 mL, 34.92 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (200 mg, 0.52 mmol) were reacted for 16 h. Purification on a silica gel column with 1:15 methanol:CH2Cl2 gave 5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine (168 mg, 0.47 mmol, 90%); MS (EI): m/z (rel. intensity) 360 (0.17, M+); 1H NMR (DMSO-d6) δ7.41 (s, 1H, Ar—H), 7.32 (s,1H, Ar—H), 6.63 (d; 1H, NH, J=7.3 Hz), 5.73 (d, 1H, CH, J=6.6 Hz), 5.26 (m, 2H, 2 overlapping OH), 4.33 (m, 1H, CH), 4.01 (m, 1H, CH), 3.91 (m, 1H, CH), 3.81 (m, 1H, CH), 1.37 (d, 3H, CH3, J=6.1 Hz), 1.21 (d, 6H, CH3, J=6.3 Hz).

Provenance & Evidence