Citric Acid → 2-Butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Participants

Reaction Steps

A solution of sodium hydroxide (1.44 g, 35.9 mmol) in water (7 mL) was added to a solution of ethyl 3-pentanimidamido-1H-pyrrole-2-carboxylate hydrochloride (2.46 g, 8.99 mmol) in ethanol (30 mL). The resultant mixture was heated at reflux for a total of 4 hours. The reaction mixture was cooled to room temperature and the pH adjusted to pH 6.5 with aqueous citric acid. The resultant mixture was extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (Na2SO4), filtered and evaporated to give the title compound as a pale brown solid (1.69 g).

Provenance & Evidence