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. Author manuscript; available in PMC: 2013 Sep 1.
Published in final edited form as: Bioorg Med Chem. 2012 Jul 14;20(17):5181–5187. doi: 10.1016/j.bmc.2012.07.006

Scheme 2.

Scheme 2

(a) (i) MsCl, Et3N, CH2Cl2, 0 °C → rt, 30 min, (ii) NaSMe, DMF, rt, 1 h, 75% (I), 91% (II); (b) aq. HCl (37%), MeOH, 0 °C → rt, 1 h, 100% (I, II and III); (c) 10, 2-picoline-borane complex (for I and II) or NaCNBH3 (for III), MeOH, Et3N (for I and II) or NaHCO3 (for III), rt, 16 h, 67% (I), 78% (II), 71% (III); (d) 7M NH3-MeOH, 135 °C, sealed tube, 24–30 h, 74% (I), 86% (II), 59% (III); (e) NH2NH2•H2O, Pd black, 7M NH3-MeOH, rt 1 h, 84% (I), 79% (II), 76% (III).