A 2-Trifluoromethyl Analog of Thiamin

Two synthetic routes for thiamin, adapted from classical methods, were found satisfactory for the preparation of 3-[(4-amino-2-trifluoromethyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium chloride hydrochloride [(VII) “trifluorothiamin”]. Solvolysis of intermediates occurred under certain conditions. “Trifluorothiamin” is biologically active as a thiamin antagonist in microorganisms and in mice where paralysis and opisthotonus occur. Growth of a transplanted carcinoma and a leukemia was suppressed in mice on a thiamin-deficient diet.