The Eenie-Meenie Reactions

Chemists at AstraZeneca have discovered a new reaction, which they have intriguingly called the Eenie Meenie reaction (Pearson S E et al, Tetrahedron Lett, 2002, 43, 1303). The reaction is the displacement by nucleophiles of an alkoxy group in a series of alkoxymethyl, diamino pyrimidines.
When 2-aminobenzyl alcohol was used as nucleophile the novel product (1) was formed by the mechanism shown below. With 4-aminobenzyl alcohol in butanol solvent, the product (2) was formed.

The name comes from the mechanism which involves “ene” and “iminium” functionalities.