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. Author manuscript; available in PMC: 2013 Jan 12.
Published in final edited form as: J Med Chem. 2011 Dec 28;55(1):342–356. doi: 10.1021/jm201229j

Scheme 4a.

Scheme 4a

Reagents and conditionsa: a) silylated 6-chloropurine, TMSOTf, DCE, rt to 80 °C, 5 h; b) NH3, MeOH, 80 °C, 2 h; c) Br2, 1 N NaOAc, MeOH, rt, 40 min; d) silylated 8-bromoadenine, TMSOTf, DCE, rt to 90 °C, 2 h; e) 1-hexyne, CuI, TEA, DMF, (PPh3)2PdCl2, rt, 3 h; f) 1 N HCl, THF, rt, 15 h; g) H2, Pd/C, MeOH, 15 h.