Methanolysis of Fluoropyridine Aminals

A series of fluoropyridines featuring a N,N,N’-trimethyl, N’-trimethylsilylaminal group were subjected to methanolysis. The methanolysis carried out at room temperature yielded a mixture of products. The aminal group was transformed into a methylimine group and ensuing dimethylamine substituted (or not) a fluorine atom. A relative content of pyridine methylimines with dimethylamino group and without it was determined for all fluoropyridines. Additionally, these compounds were hydrolyzed into aldehydes. This work presents a novel and efficient methodology for synthesizing important scaffolds found in various drug candidates and biologically relevant compounds.