Beaker faces wrath of Dimroth rearrangement

At the end of 2006 I was messing around with some 1-alkyl-2-aminopyrimidinium-based ligands of type 1 in aqueous solution. For some reason, my ligands were giving weird NMR spectra after heating in water. Turns out Beaker the ignoramus was unaware of some old-school chemistry pioneered by Dimroth in the early 1900's, which predicts the formation of rearranged product 2. This has the alkyl group now stuck to the amino nitrogen atom rather than the pyrimidine nitrogen. The simple hydrolysis and condensation mechanism is depicted below.The reaction is very general - it can occur in a heap of nitrogen heterocycles in which an amino group is alpha to an endocyclic nitrogen atom. So yeah, its back to the drawing board for me =(

-Bkr