Pyridyl N-oxide derivatives of hydroxyl terminated polybutadiene-pyridine (HTPB-PY) were synthesized via functionalization on terminal carbon atoms of HTPB backbone by 2-chloropyridine and epoxidation of C=C bonds and N atoms using in situ generated dimethyl dioxirane (DMD). (HNMR)-H-1, (CNMR)-C-13, (NNMR)-N-14, and FT-IR spectroscopy techniques used in order to investigate the structural elucidation of products. In this synthesis method, HTPB terminal hydroxyl groups have preserved unchanged without applying any conditional controllers.