Pyrimidines. Part IV. The preparation of some analogues of vitamin B6

Abstract

5-Hydroxymethyl-4-methyl-2-methylthiopyrimidine (III) was converted into the corresponding 4-formyl derivative (VI), an analogue of pyridoxal, by the Ortoleva–King procedure. Reduction of (VI) gave the pyridoxol analogue, 4,5-bishydroxymethyl-2-methylthiopyrimidine (VII). Attempts to prepare the pyridoxamine analogue, 4-aminomethyl-5-hydroxymethyl-2-methylthiopyrimidine (I), by treatment of 4-hydroxyiminomethyl-5-hydroxymethyl-2-methylthiopyridimine (IX), 5-acetoxymethyl-4-cyano-2-methylthiopyrimidine (XIV), and 4-carbamoyl-5-hydroxymethyl-2-methylthiopyrimidine (XVIII) with lithium aluminium hydride led to ring reduction and/or reduction of the group in the 5-position with formation of 1,6-dihydropyrimidines or 5-methylpyrimidines.