Due to the biological importance of thienopyrimidine derivatives, we present here a synthetic way for the design of new thienopyrimidines (2‒11) using the precursor 2-(4-Oxo-9-phenyl-7-(p-tolylamino)-3,4-dihydropyrimido[4′,5′:4,5]thieno[2,3-d] pyrimidine-2-yl)acetohydrazide 1. Spectral analyses techniques (IR,¹H NMR, and ¹³C NMR) were utilized to confirm the structures of all synthesized compounds. All the new compounds were screened for their anti-bacterial and anti-inflammatory activity showing significant results compared to the standard drug. A molecular docking approach was utilized to investigate the proposed molecular mechanism of the antibacterial and anti-inflammatory activity of the synthesized compounds. Drug-like properties were analyzed to highlight the potential oral drug candidates.