1,1'-Carbonyldiimidazole → 5-Amino-4-(3-{3-[(tert-butoxycarbonyl)amino]propyl}ureido)-1-methylpyrazole

Participants

Reaction Steps

To a suspension of 1,1′-carbonyldiimidazole (1.94 g) in methylene chloride (20 ml) was added tert-butyl N-(3-aminopropyl)carbamate (2.30 g), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added N-ethyldiisopropylamine (2.56 g) and 4,5-diamino-1-methylpyrazole sulfuric acid salt, (2.10 g), and the mixture was stirred at 30° C. for 3 days. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 6% methanol/chloroform to give 5-amino-4-(3-{3-[(tert-butoxycarbonyl)amino]propyl}ureido)-1-methylpyrazole (1.75 g) as a solid.

Provenance & Evidence