Acetic Acid → 4-{[(6-Butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide

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Reaction Steps

5-Aminoimidazole-4-carboxamide (0.30 g, 2.4 mmol) was added to the solution of 6-butoxypyridine-2-carbaldehyde (0.43 mg, 2.4 mmol, obtained from Example 17(d)) in anhydrous ethanol (30 mL) and the reaction mixture was refluxed. After 2 h, the reaction mixture was concentrated in vacuo. The light pink solid was suspended in anhydrous ethanol (25 mL), and acetic acid (0.27 mL, 4.8 mmol) was added. After 1.5 h, sodium cyanoborohydride (0.30 g, 4.8 mmol) was added to the mixture. After stirring o.n. at ambient temperature, the reaction mixture was concentrated in vacuo. The resulting 1.2 g of crude title compound was used in the next step without further purification. MS (ESI) m/z 290 (M+1)

Provenance & Evidence