Ammonia → 2-(3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1, 2, 3, 5]tetrazin-8-yl)thiazole-4-carboxamide

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To a solution of 3-(imino(3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)methylthio)-2-oxopropanoic acid (0.700 g; 2.5 mmol) in dry THF (30 mL) under nitrogen was added isobutyl chloroformate (0.50 mL; 3.8 mmol), followed by triethylamine (0.53 mL; 3.8 mmol). The mixture was stirred for 1 hour, and then ammonia solution (0.5 M in dioxane; 20 mL) was added, and stirring continued for a further 3 hours. The precipitate was filtered, washed with water (5×20 mL) and diethyl ether (2×15 mL) to yield the title compound as a pale yellow solid (0.223 g; 40%). δH (DMSO-d6) 8.94 (1H, s), 8.42 (1H, s), 7.74 (1H, bs), 7.59 (1H, bs), 3.89 (3H, s).

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