4,6-Diamino-2-bromo-3-pyridinecarbonitrile → 4,6-Diaminonicotinonitrile

Participants

Reaction Steps

A solution of (II) (15.1 g, 0.071 mol), KOAc (7.0 g, 0.071 mol) and 5% Pd/C (4 g) in THF (tetrahydrofuran) (130 mL) and MeOH (methanol) (70 mL) was hydrogenated (55 psi/20° C.) for 7 days. The resulting solution was filtered over Celite, washing with THF/MeOH, then the solvents were removed under reduced pressure. The residue was dissolved in dilute HCl, then the solution neutralised with 40% NaOH and excess Na2CO3 to give 3-cyano-4,6-diaminopyridine (III) (6.58 g, 69%): mp (water) 197-198° C. [Metzger R., Oberdorfer J., Schwager C., Thielecke W., Boldt P., Liebigs Ann. Chem., 1980;946-953 record mp (benzene) 205° C⟧

Provenance & Evidence