Studies on Pyrimidine Derivatives and Related Compounds. LII. Reaction of Thiamine with Phosphites. (1)

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Syntheses of dialkyl 2-{3-(2-methyl-4-aminopyrimidin-5-yl) methyl-3a-methylperhydrofuro-[2,3-d]-thiazole} phosphonates (Va-f), and their thermal isomerization affording dialkyl 7-[2,9a-dimethyl-9-(2-hydroxyethyl)-5,6,7,9,9a, 10-hexahydropyrimido [4,5-d]-thiazolo [3,4-a] pyrimidine] phosphonates (VIIa-f) are described. Transesterification was occurred in the reaction of thiamine (B_1) with diphenyl hydrogen phosphite in methanol. Regeneration of V from VII was also detected. O-allyl 7-[2,9a-dimethyl-9-(2-hydroxyethyl)-5,6,7,9,9a, 10-hexahydropyrimido [4,5-d] thiazolo [3,4-a] pyrimidine] phosphinic acid (IX), O-allyl 2-[3-(2-methyl-4-aminopyrimidin-5-yl) methyl-4-methyl-5-(2-hydroxyethyl) thiazoline (4)] phosphinic acid (X), methyl and ethyl 2-[3-(2-methyl-4-aminopyrimidin-5-yl) methyl-3 a-methylperhydrofuro [2,3-d] thiazole] phenylphosphonate (XIIa-b) were obtained. Brief reaction mechanisms are discussed.
社団法人日本薬学会の論文
1968-09-25