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.