Schiff bases are aldehydelike compounds in which an imine group replaces the carbonyl group. They are widely used for industrial purposes and also exhibit a broad range of biological activities. This study represents the synthesis of a new series of (E) -N-benzylidene-5-bromo-2-chloropyrimidin-4-amine derivatives (6a-l). The newly synthesized compounds were characterized by different spectral studies. All these new compounds screened for their anti-inflammatory, antimicrobial and in vitro antioxidant activities. Structure–activity relationship analysis demonstrates that hydroxyl groups on the aromatic ring contribute critically to the antioxidant activity. Compounds 6k, 6j, 6dand 6e showed significant radical scavenging and compounds 6d, 6e and 6f showed good antimicrobial and anti-inflammatory activities.