Heterocycles related to Nucleotides. VI. Photochemistry of Thiopyrimidines : Photoreduction of Thiouracils and Thiouridines with Sodium Borohydride

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On ultraviolet irradiation in the presence of sodium borohydride, 4-thiouracil (1a), 4-thiouridine (1b) and 2-thiouracil (3a) were readily reduced to 2-oxohexahydropyrimidine (2a), its riboside (2b) and 1-(3-hydroxypropyl) thiourea (4), respectively. By controling the energies of the ultraviolet light in the region below 300 nm the selective photoreduction of these thiopyrimidines was demonstrated, while uracil and uridine were unaffected under these conditions. Photochemical behavior of the thiopyrimidines was discussed.

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