Pyridine → HCID 58500140, compound

Participants

Reaction Conditions

Reaction Steps

Aminomalononitrile p-toluenesulfonate (1.00 g, 3.95 mmol), pyridine (0.32 mL, 3.95 mmol), and trimethyl orthovalerate (1.36 mL, 7.90 mmol) were combined in acetonitrile (16 mL), and the solution was heated at 85° C. for 1 hour. 3-Aminopentane (0.7 mL, 6 mmol) was added, and the reaction was heated for 1 hour and ten minutes and then allowed to cool to room temperature overnight. The solvent was removed under reduced pressure, and the resulting oil was partitioned between aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate layer was separated and washed with aqueous sodium bicarbonate, water, and brine. The combined aqueous fractions were extracted with ethyl acetate, and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.04 g of crude 5-amino-2-butyl-1-(1-ethylpropyl)-1H-imidazole-4-carbonitrile as a brown oil. 1H-NMR (300 MHz, CDCl3) δ 3.90-3.78 (m, 1H), 3.71 (br s, 2H), 2.55 (m, 2H), 0.95 (t, J=7.3, 3H), 0.86 (t, J=7.4, 6H); MS (ESI) m/z (M+1)+235.

Provenance & Evidence