Syntheses of 5-Alkenylpyrimidines by Organotin Reactions.

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Abstract
5-Stannylpyrimidines can be prepared from the corresponding bromides by lithiation at -95.degree. C and quenching with tributylstannyl chloride. The 5-stannyl-pyrimidine is used in Pd-catalyzed coupling reactions with vinyl bromides. The opposite reaction sequence, i.e. Pd-catalyzed coupling between 5-halopyrimidines and vinyltin derivatives, is also described. Alternatively, the 5-vinylpyrimidines have been obtained by dehydrohalogenation with cesium fluoride and by a modified Wittig reaction. 2-Methylthiopyrimidines are transformed into the 2-methoxy derivatives or 2-pyrimidinones using chloramine-T (CAT) in a simple one-pot synthesis.