Many coumarin derivatives have been reported to possess antimicrobial and antiproliferative activity. In view of this series of 3-(2-amino-6-substituted pyrimidin-4-yl)-2H-chromen-2-one derivatives and 3-[3-(substituted amino)propanoyl]-2H-chromen-2-one derivatives were synthesised and characterized by FT-IR, 1H-NMR and ESIMS spectrometry. Molecular docking was carried out on epidermal growth factor receptor protein, a good target for many cancers using Autodock vina. In vitro antimicrobial studies were carried out on two gram-positive organisms viz. Bacillus Subtilis and Staphylococcus Aureus and two gram-negative organisms viz. Escherichia Coli and Pseudomonas Aeruginosa. In vitro cytotoxicity studies were carried out on HeLa cell lines. Compounds from PYR series possess moderate antimicrobial and antiproliferative activity. PYR10, was found most active amongst synthesised compounds.