HCID 9998883, compound → HCID 3000382, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-tert-butylthio-5-ethyl-6-methyl-3-(2-napthylmethylamino)pyridine (98 mg, 0.27 mmol) and pyridine hydrochloride (0.45 g, 3.8 mmol) was heated under an atmosphere of nitrogen at 140° C. until evolution of gas ceased (about 45 minutes). Water was added and the resultant mixture was extracted three times with chloroform. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (15 torr). The residue was then subjected to column chromatography on silica gel (eluted with 2% methanol in ethyl acetate). Collection and concentration of appropriate fraction yielded 32 mg (36%) of the pyridinethione. Anal. Calcd for C19H20N2S·0.25 EtOAc: C, 72.68; H, 6.71; N, 8.48. Found: C, 72.41; H, 6.59; N, 8.86.

Provenance & Evidence