What else do you have in the molecule?
I've had some success forming the aluminium amide from amines with AlMe3 (careful, rather pyrophoric), at around 0 deg C in dry toluene, then adding a methyl ester to form the amides and allowing to slowly warm to rt.
My molecule had a 2-chloropyrimidine in it as well, that was untouched (no evidence rom LC-MS / 1H NMR etc), so I guess it's reasonably robust, maybe it was just favoured at the lower temperature compared to the chlorine displacement.