2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-(6-(Pyridin-2-yl)-1,2,4,5-tetrazin-3-yl)pyridin-3-amine

Participants

Reaction Steps

To a solution of 3-(5-aminopyridin-2-yl)-6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine (0.950 g, 3.8 mmol) in anhydrous toluene (25 mL) under N2 was added 2,3-dichloro-5,6-dicyanobenzoquinone (1.7 g, 7.5 mmol). The reaction mixture was allowed to reflux and stir for 12 hr. The reaction mixture was concentrated under reduced pressure, and the crude residue was concentrated in vacuo onto deactivated silica gel and chromatographed using a gradient (0-100%) of acetone in hexanes to give 771 mg (3.1 mmol, 81%) of the title compound as a red solid, mp 207-209° C.

Provenance & Evidence