1H-1,2,4-Triazole → 7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidine

Participants

Reaction Steps

To a solution of 1H-[1,2,4]triazole (2.2 g, 31.9 mmol) in anhydrous N,N-dimethylformamide (20 ml) under a nitrogen atmosphere was added sodium hydride (1.18 g, 29.4 mmol, 60% dispersion in oil) with caution in a portionwise manner. This mixture was then stirred for 20 min at room temperature. To a separate solution of 7-chloromethylimidazo[1,2-α]pyrimidine hydrochloride (5.0 g, 24.5 mmol), also dissolved in N,N-dimethylformamide (50 ml) under nitrogen, was added potassium carbonate (6.76 g, 49.0 mmol) and the mixture stirred for 5 min at room temperature. To the 7-chloromethylimidazo[1,2-α]pyrimidine solution was added the triazole sodium salt as a solution in N,N-dimethylformamide and the mixture stirred at room temperature for 16 h. Solvent was removed under reduced pressure and the resulting residue purified by flash column chromatography on silica eluting with dichloromethene, methanol and aqueous ammonia solution (33%) in the ratios 90:5:0.5 respectively to give 7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidine (3.38 g, 69%) as a tan solid: δH (360 Mz, d6-DMSO) 5.63 (2H, s), 6.90 (1H, d, J 7), 7.71 (1H, d, J 1.3), 7.91 (1H, d, J 1.4), 8.04 (1H, s), 8.73 (1H, s), 8.97 (1H, d, J 7); m/z (ES+) 201 (M++H).

Provenance & Evidence