Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone

Abstract

Three novel 5-(2-haloethyl)pyrimidine derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, MS, IR spectra and elemental analysis. Iodine and chlorine atoms in the C-5 side chain were introduced by reaction of 5-(2-hydroxyethyl)pyrimidine with hydroiodic acid and phosphoryl chloride, respectively. The structure of the intermediate α-(1-carbamyliminomethylene)-γ-butyrolactone was determined by X-ray crystal structure analysis. The molecule deviates very slightly from planarity. Three N−H···O hydrogen bonds link the molecules into one-dimensional chains of edge-fused rings.

Keywords

• 5-(2-Haloethyl)pyrimidine
• Synthesis
• X-ray crystal structure
• Hydrogen bonds