1 research outputs found
Regioselective Control of the S<sub>N</sub>Ar Amination of 5‑Substituted-2,4-Dichloropyrimidines Using Tertiary Amine Nucleophiles
The
S<sub>N</sub>Ar reaction of 2,4-dichloropyrimidines, further
substituted with an electron-withdrawing substituent at C-5, has selectivity
for substitution at C-4. Here we report that tertiary amine nucleophiles
show excellent C-2 selectivity. In situ N-dealkylation of an intermediate
gives the product that formally corresponds to the reaction of a secondary
amine nucleophile at C-2. This reaction is practical (fast under simple
reaction conditions, with good generality for tertiary amine structure
and moderate to excellent yields) and significantly expands access
to pyrimidine structures