Diisopropylethylamine → 7-Chloro[1,2,4]triazolo[1,5-a]pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of hydroxylamine hydrochloride (5.35 g, 77.0 mmol, Eq: 5) and N-ethyldiisopropylamine (5.97 g, 8.07 ml, 46.2 mmol, Eq: 3) in ethanol (80 ml) was stirred for a few minutes at 25° C., then the mixture was added to 1-ethoxycarbonyl-3-(4-chloro-pyridin-2-yl)-thiourea (4.0 g, 15.4 mmol, Eq: 1.00) and the resulting mixture was refluxed for 2.5 days (over the weekend). The crude material was applied on SiO2 and purified by flash chromatography over a 20 g SiO2 column using ethyl acetate 100% as eluent affording 7-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (2.03 g/78.2%) as a white solid. MS: m/e=169.1 (M+H+), mp: 189-190° C.

Provenance & Evidence