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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 6.

Scheme 6

Attempted synthesis of a 7-deazapurine analog: Reagents and conditions: (a) NIS, DMF, rt, 18 h; (b) 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (TBR), BSA, TMSOTf, MeCN, reflux, 2 h; (c) NH4OH, 1,4-dioxane, 60 °C, 3 d; (d) H2, Pd/C, Et3N, DMF; (e) Me2C(OMe)2, p-TsOH; (f) TBSCl, imidazole, rt, 18 h; (g) Boc2O, DMAP, Et3N, DMF; (h) TBAF; (i) MsCl, Et3N, CH2Cl2, 0.5 h; (j) MeNH2/EtOH, 50 °C, 18 h; (k) 12, NaI, Et3N, MeCN, rt, 18 h.