1,1'-Carbonyldiimidazole → 7-Methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazin-4(1H)-one

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Reaction Conditions

Reaction Steps

N-[2-Methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]imidoformamide (58.3 g, 285 mmol) was combined with 1,1′-carbonyldiimidazole (98%, 59.0 g, 357 mmol) in tetrahydrofuran (1140 mL) at 63° C., and the suspension was stirred for 2.5 hours at 65° C. The mixture was cooled and concentrated in vacuo; the resulting solid was slurried with methanol (400 mL), warmed to reflux for 20 minutes and cooled to 7° C. The solid was collected to provide C1 as a pale yellow solid. Yield: 45.9 g, 199 mmol, 70%. LCMS m/z 231.1 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.48 (s, 3H), 3.88 (s, 3H), 7.79 (s, 1H), 8.08 (s, 1H), 8.37 (s, 1H), 11.59 (br s, 1H).

Provenance & Evidence