Methyl 1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-benzo[d]imidazole-7-carboxylate: a combined X-ray and DFT study

Abstract

The title compound, C16H16N4O3, was obtained as a side product during the synthesis of the previously reported antitubercular agent N-(2-fluoroethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-1H-benzo[d]imidazole-4-carboxamide and structurally characterized by X-ray crystallography and computational methods. In the crystal (space group P21/n, Z = 4), the title compound adopts a twisted conformation with a dihedral angle between the benzimidazole and pyrimidine mean planes of 84.11 (3)°. The carboxylate group and the 5-methyl group on the pyrimidine ring exhibit partial disorder. The DFT-optimized molecular structure resembles the structure of the minor component in the crystal.

Keywords

• crystal structure
• dft calculations
• benzimidazole
• pyrimidine
• tuberculosis