Syntheses and Structures of Substituted [4-(2,2,2-Trifluoroethoxy)-2-Pyridinyl]-Methylthio-Imidazoles and -Pyrimidines

Abstract

Reactions of substituted 2-(chloromethyl)-pyridine (1a–1b) and substituted imidazole-2-thione (2a–2c) in the presence of sodium methoxide afforded a series of substituted [4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methylthio-imidazoles (3a–3f) in good yields. Similar reactions of compounds 1a–1b with different pyrimidine-2-thiol (4a–4b) led to the corresponding [4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methylthio-pyrimidine (5a–5d, av. 90 %) derivatives. Molecular structures of compounds 3a and 5b were confirmed by single-crystal X-ray diffraction analyses. The unit cells of both compounds have monoclinic P2₁/c symmetry with the cell parameters a = 7.786(7), b = 21.910(19), c = 8.675(8) Å, β = 91.113(13)°, and V = 1480(2) Å³ for 3a and a = 9.1683(13), b = 14.0946(19), c = 12.5409(18) Å, β = 93.686(2)°, and V = 1617.2(4) Å³ for 5b.

Graphical Abstract

A series of substituted [4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methylthio-imidazoles and -pyrimidines were synthesized and characterized, of which structures of 3-methyl-[4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methylthio-1-methyl-imidazole and 3-methyl-[4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methylthio-4,6-dimethyl-pyrimidine were confirmed by X-ray crystallography.