Hydrochloric Acid → 1-[(6-Oxo-1,6-dihydropyridin-2-yl)methyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

Participants

Reaction Steps

Benzoyl isothiocyanate (0.27 g, 1.6 mmol) dissolved in CH2Cl2 (3 mL) was added to 3-{[(6-oxo-1,6-dihydropyridin-2-yl)methyl]amino}-1H-pyrrole-2-carboxylic acid ethyl ester (0.25 g, 0.96 mmol) in CH2Cl2 (7 mL). The resulting mixture was stirred at r.t. overnight. The solvent was removed in vacuo and the residue was dissolved in methanol (15 mL) and potassium carbonate (0.50 g, 3.6 mmol) was added. The reaction mixture was stirred at 50° C. for 6.5 h. After cooling to r.t., 1M HCl was added dropwise until a neutral pH was obtained. The resulting precipitate was collected, washed with methanol and purified by preparative HPLC to obtain the title compound (0.097 g, 37%) as a solid.

Provenance & Evidence