Acetic Acid → 4-[(2-ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide

Participants

Reaction Steps

NaCNBH3 (0.077 g, 1.23 mmol) was added to 5-amino-4-imidazolecarboxamide hydrochloride (0.200 g, 1.23 mmol) and acetic acid (141 μL, 2.46 mmol) in methanol (1.5 mL). 2-Ethoxy-2-methylpropanal (0.286 g, 2.46 mmol) obtained from Example 1(b) was added drop by drop. After 1.5 h more 2-Ethoxy-2-methylpropanal (0.300 g, 2.58 mmol) was added followed by more 2-Ethoxy-2-methylpropanal after 0.5 h (0.424 mg, 3.65 mmol). The reaction mixture was stirred at r.t. 17 h after which it was concentrated and purified by flash silica gel chromatography (CHCl3/MeOH; 20:1-9.1), to give the title compound as an oil in 90% yield (0.251 g). MS (ESI) m/z 227 (M+1).

Provenance & Evidence