The clinical significance of pyran and pyrimidine condensed systems and the raise in problem of multidrug resistant bacterial pathogens has directed us to synthesize pyranopyrimidine derivatives via the reactions of the versatile, 2-amino-4-(4-methoxyphenyl)-4H-substituted chromene-3-carbonitrile with the appropriate reagents. The newly synthesized compounds were characterized by IR, (1)H NMR, (13)C NMR, Mass spectra and Elemental analysis. The compounds were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv [ATCC-27294] and antibacterial activity against Staphylococcus aureus [ATCC-25923] and Streptococcus pyogenes [MTCC-443] as gram-positive, Escherichia coli [ATCC-25922] and Pseudomonas aeruginosa [MTCC-441] as gram-negative bacterial strains and antifungal activity against Aspergillus niger [MTCC-282]. Several derivatives exhibited pronounced antitubercular and antimicrobial activities.