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. Author manuscript; available in PMC: 2023 Feb 10.
Published in final edited form as: J Med Chem. 2022 Jan 26;65(3):2409–2433. doi: 10.1021/acs.jmedchem.1c01852

Scheme 5. Introduction of a Distal Urea-Type Substituent on the 4-Benzyloxyimino Group of the Pyrimidine Scaffold, to Potentially Enhance H-Bonding in That Region of the CD73 Binding Sitea.

Scheme 5.

a Reagents and conditions: (i) EtOH, reflux, 12 h, 72%; (ii) acetic anhydride, Et3N, DMAP, CH3CN, 10 min, rt, 95%; (iii) MeI, DMAc, rt, 4 h, 95%; (iv) 69, Et3N, THF, reflux, 12 h, 72%; (v) NH3/MeOH, rt, 12 h, 87%; (vi) methylenebis(phosphonic dichloride), (CH3O)3PO, 0 °C, 3 h, 8.4%.