An unexpected replacement of a methyl with an amino in the tetramethylpyrazine system.

A novel and unexpected product, 5-amino-3,6-dimethyl-2-pyrazinecarbonitrile ( 3), was obtained during the attempted to synthesis of 3,5,6-trimethyl-2-pyrazinecarbonitrile ( 2) from its corresponding alcohol ( 1) by the catalytic amount of KI or I in combination with TBHP as an external oxidant. The product was confirmed by ESI-MS, HRMS, H-NMR, C-NMR, and 2D-NMR. The mechanism for the formation of the amino group in the tetramethylpyrazine system is also proposed. [ABSTRACT FROM AUTHOR]