Abstract
The new compound, Substance X, formed from thiamine hydrochloride and 4 molar equivalents of sodium hydroxide, forms an N-acylated compound by introduction of acyl group into the amino group in 4-position of the pyrimidine ring by acylation. It is decomposed into 2-methyl-4-amino-5-pyrimidinylmethanesulfonic acid (VIII) and Substance Y (C10H17O2NS) by the action of sodium sulfite, and Substance Y forms an N-monoacetate by acetylation. The structure of Substance X was assumed to be 2-(2-hydroxyethyl)-3-hydroxy-3, 4a-dimethyl-4-[(2-methyl-4-amino-5-pyrimidinyl)-methyl]perhydrofuro[3, 2-b]-1, 4-thiazine (IX) from the fact that it is produced quantitatively from the diazepine compound (II) and α-mercapto-ketone compound (III) in the presence of alkali, some thiazole compounds possessing 2-hydroxyethyl group in 5-position have tendency to undergo facile cyclization to a tetrahydrofuran ring, and from other reactions. Consequently, formula (X) is proposed for the Substance Y and (XI) to its monoacetylated compound. The dihydro compound obtained by reduction of Substance X would be given the formula (XII) and its acetylation products would be (XIII) and (XIV). Docomposition of (XII) with sulfite would give (VIII) and (XV), and acylation of (XV) would produce (XVI). Attempted preparation of (IX) by deformylation of (XIX) was not effected.
