Diisopropylethylamine → 6-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine

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Reaction Steps

To 5-methoxypyridin-2-amine ethoxycarbonyl thiourea (10.21 g, 40 mmol) in ethanol (57 mL) and methanol (57 mL) was added hydroxylamine hydrochloride (14 g, 200 mmol) and Hunig's Base (21 mL, 120 mmol). The mixture was stirred at room temperature for 2 hours, and then heated at 60° C. for 4 hours. The reaction was cooled to room temperature and filtered to remove solids. It was concentrated in vacuo and then suspended in chloroform. The solids were filtered off to yield 6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine (6.05 g, 33.2 mmol, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.30 (1 H, d, J=1.83 Hz), 7.24-7.32 (1 H, m), 7.16-7.23 (1 H, m), 5.82 (2 H, br. s.), 3.78 (3 H, s). MS (LC/MS) R.T.=0.53; [M+H]+=165.2.

Provenance & Evidence