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. Author manuscript; available in PMC: 2018 Oct 15.
Published in final edited form as: Bioorg Med Chem. 2017 Aug 3;25(20):5433–5440. doi: 10.1016/j.bmc.2017.07.063

Scheme 5.

Scheme 5

Attempted synthesis of a dideazapurine analog: Reagents and conditions: (a) Hydrazine, Ru/C, EtOH, reflux, 3 h; (b) formic acid, reflux, 18 h; (c) TAR, BSA, TMSOTf, MeCN, reflux, 3 h; (d) NH3/MeOH; (e) Me2C(OMe)2, p-TsOH, 55 °C, 2 h; (f) TBSCl, imid., CH2Cl2; (g) Fe, FeSO4, MeOH/H2O, 50 °C, 2 h; (h) Boc2O, DMAP, Et3N, DMF; (i) TBAF, THF; (j) MsCl, Et3N, CH2Cl2; (k) MeNH2/EtOH, 50 °C, 18 h; (l) 13, NaI, Et3N, MeCN, rt, 6 h.