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Note | Regular issue | Vol 48, No. 12, 1998, pp.2601-2610
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8270
Reactivity of Dimethylphenylsilyllithium toward 5- and 6-Substituted 1,3-Dimethyluracil Derivatives

Raffaele Saladino,* Luigi Stasi, Gabriele Volpe, Rosario Nicoletti, and Maurizio Botta*

*Dipartimento Agrochimico, Universita degli studi di Viterbo "La Tuscia", Via San Camillo de Lellis, 01100 Viterbo, Italy


Dimethylphenylsilyllithium (PhMe2SiLi) reacts with 5-substituted 1,3-dimethyluracils by selective addition at the electrophilic C-6 position of the uracil ring to give the corresponding 6-dimethylphenylsilyl-5,6-dihydrouracil derivatives. The reaction of PhMe2SiLi with 6-substituted 1,3-dimethyluracils showed a different selectivity, and an unusual addition at the C-5 position was observed. This synthetic procedure appears to be an efficient entry to a new class of highly functionalized 5,6-dihydro-1,3-dimethyluracils characterized by the presence of a silicon substituent selectively introduced at the C-5 and C-6 positions of the uracil ring.