C[O:2][C:3](=O)[CH2:4][N:5]([CH2:14][C:15]1[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[H-].[Na+]>CS(C)=O.O>[Br:21][C:19]1[CH:18]=[N:17][C:16]2[NH:22][C:3](=[O:2])[CH2:4][N:5]([CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH2:14][C:15]=2[CH:20]=1A solution of [(2-amino-5-bromo-pyridin-3-ylmethyl)-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester (0.34 g, 0.88 mmol) in DMSO (10 mL) was treated with NaH (60% dispersion in mineral oil, 35 mg, 0.88 mmol). After stirring at room temperature overnight, the mixture was diluted with H2O (20 mL), and then extracted with EtOAc (4×50 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The resulting pale yellow oil was purified by flash column chromatography (silica gel, CH2Cl2,/MeOH, 97:3 to 90:10) to give the title compound (0.24 g, 57%) as an off-white solid: MS (ESI) m/e 355 (M+H)+.
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