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. Author manuscript; available in PMC: 2021 Sep 10.
Published in final edited form as: J Med Chem. 2020 Aug 21;63(17):9977–9989. doi: 10.1021/acs.jmedchem.0c01111

Scheme 1. Synthesis of PRMT5 Putative Degraders 9–13a.

Scheme 1.

aReagents and conditions: (a) i-PrOH, reflux; (b) TFA, DCM; (c) EDCI·HCl, HOAt, NMM, 6-chloropyrimidine-4-carboxylic acid, DMSO, 18% over three steps; (d) tert-butyl 3-aminoazetidine-1-carboxylate, NMP, 90%; (e) dicarboxylic acids, EDCI·HCl, HOAt, NMM, DMSO, 54–78%; (f) 3, EDCI·HCl, HOAt, NMM, DMSO, 36–60%.