Diethylamine → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid diethylamide

Participants

Reaction Steps

Diethylamine (0.400 mL) was suspended in tetrahydrofuran (2.00 mL) and cooled in an ice bath. This solution was charged with trimethylaluminum (0.500 mL of a 2 M solution in heptane). After 20 minutes the reaction was charged with the 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester, prepared as in Example 16, Step 1, (0.255 g, 0.720 mmol) and shaken. After 18 hours the reaction was diluted with 1 volume of ethyl acetate and treated with an equal amount saturated aqueous sodium/potassium tartrate. After 6 hours the organic layer was isolated, dried over magnesium sulfate and concentrated to afford the desired product 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid diethylamide, MS (APCI+): m/z 382.1 (M+H).

Provenance & Evidence