A new route to Septorin via controlled metalations of pyrazines. Diazines XXX

The metalation of 2-chloro-3-(1-hydroxy-4-alkoxyphenylmethyl)pyrazines with LTMP in tetrahydrofuran has been studied and afforded regioselectively functionalized compounds at C6. This regioselectivity was established by application of gradient enhanced HMBC sequence for the observation of long range 1H–15N heteronuclear couplings at natural abundance and by X-ray diffraction. Associated with the regioselective metalation at C6, the transition metal catalyzed cross coupling reaction provides a new pathway to Septorin.