Phosphorus oxychloride → 3-Methyl-8-(5-phenyloxazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

3-Methyl-4-oxo-N-(2-oxo-2-phenylethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (0.180 g; 0.58 mmol) was added to phosphorus oxychloride (3.6 mL) and the stirred mixture heated at 110° C. for 1.5 hours. The mixture was cooled and poured onto ice, and allowed to stand for 3 hour. The solid was filtered and extracted with chloroform on Soxhlet apparatus. Concentration under reduced pressure yielded pure title compound as a bright yellow powder (55 mg; 32%). δH (DMSO-d6) 8.94 (1H, s), 7.99 (1H, s), 7.85 (2H, m), 7.55 (2H, m), 7.44 (1H, tt, J=7.8, 1.1), 3.90 (3H, s).

Provenance & Evidence