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Synthesis 1990; 1990(9): 761-763
DOI: 10.1055/s-1990-27007
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Preparation of 5-Substituted 2-Mercapto-1-methylimidazoles. Direct Metalation of 2-Mercapto-1-methylimidazole

Brian T. Phillips* , David A. Claremon, Sandor L. Varga
  • *Department of Medicinal Chemistry, Merck Sharp & Dohme Research Laboratories, West Point, PA 19486, USA
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Publication Date:
17 September 2002 (online)

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2-Mercapto-1-methylimidazole (1) is directly metalated with tert- butyllithium in tetrahydrofuran to give the 5, S-dianion 2. Reaction of the dianion 2 with a series of electrophiles gives regioselectively 5-substituted 2-mercapto-1-methylimidazoles 4, 5 and 7.

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