Imatinib: spot the conditions flaw

Single question

Final SNAr coupling in the imatinib synthesis: a 2-methyl-5-aminoaryl benzamide attacks the chloride of 4-chloro-2-(pyridin-3-yl)pyrimidine. The reactants and target are right. Check the temperature and the catalyst.

SNAr on chloropyrimidines

Acid catalysis in pyrimidine SNAr

Imatinib (Novartis) process chemistry

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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