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  • Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Journal of the American Chemical Society (2010-01-26)
Nicholas R Perl, Nathan D Ide, Sudeep Prajapati, Hahdi H Perfect, Sergio G Durón, David Y Gin
RESUMEN

A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

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Sigma-Aldrich
2-Aminopyrimidine, 97%