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Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation


The palladium-catalyzed carbonylation of iodoferrocene was investigated in the presence of 2-aminopyrimidine derivatives as nucleophiles. 2-Amino-4-hydroxy-6-methylpyrimidine was found to act both as an O- and an N-nucleophile, leading to an ester and an amide derivative, respectively. Together with other spectroscopic methods, the structure of both products was proved by X-ray crystallography. 2-(Ferrocenoylamino)-4-chloro-6-alkylpyrimidines were obtained during carbonylation of iodoferrocene and 2-amino-4-chloro-6-alkylpyrimidines. The formation of a dimeric product via two subsequent carbonylation steps was also observed. The products may have practical importance as electrochemically detectable biosensors or building blocks for supramolecular assemblies.

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The authors thank the Hungarian National Science Foundation (OTKA K105632) and COST Action CM1005 for financial support. Mrs B. Norberg is acknowledged for technical assistance during X-ray diffraction analysis.

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Correspondence to Rita Skoda-Földes.

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Fehér, C., Habuš, I., Wouters, J. et al. Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation. Monatsh Chem 145, 1981–1986 (2014).

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  • Metallocenes
  • Heterocycles
  • Homogeneous catalysis
  • Crystal structure