p-Toluenesulfonic acid → Diethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine

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Reaction Steps

A solution of 0.29 g (0.001 mol) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine in 50 ml dimethylformamide was treated with 0.05 g (0.001 mol) sodiumhydride(55%) for 15 minutes at room temperature. Then 0.22 g (0.001 mol) ethyl-p-toluenesulfonate were added and stirring was continued for 22 hours. Addition of sodiumhydride and p-toluenesulfonate was repeated three times. After each addition stirring was continued at 50° C. for 20 hours. Saturated aqueous sodiumbicarbonate was added and the mixture was extracted with dichloromethane. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 96/4 gave 0.05 g (15%) diethyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as yellow oil. MS m/e (%): 343 (M+, 59), 314 (100), 300 (73), 104 (51).

Provenance & Evidence