Lithiation and Thiylation of 5-Bromopyrimidines.

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Abstract
5-Thiylated pyrimidines have been prepared by cyclization reactions, and by reactions involving lithiated pyrimidine intermediates. tert-Butyldimethylsilyl, trimethylsilyl, isopropy and tert-butyl groups have been tried as O-protecting groups in the lithiation of 5-bromo-2(1H)-pyrimidinone. The trimethylsilyl group is cleaved during lithiation and the tert-butyldimethylsily group is cleaved by thiolates generated from disulfides during the thiylation. tert-Butyldimethylsilyl chloride together with a base in dichloromethane was used for O-silylation of pyrimidin-2-ones. tert-Butyldimethylsilyl 2-pyrimidinyl ethers are cleaved by acetic acid in chloroform.

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