[CH3:1][Mg]Br.[CH3:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([C:20]#[N:21])=[C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:12]=2)[CH:7]=[CH:6]1.[BH4-].[Na+]>C1COCC1>[CH3:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([CH:20]([NH2:21])[CH3:1])=[C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:12]=2)[CH:7]=[CH:6]1Methylmagnesium bromide (3.0 M in THF, 0.60 mL, 1.8 mmol) was added to a stirred solution of 1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (145 mg, 0.60 mmol) in dry THF (6 mL) at RT. The reaction mixture was stirred for 1 h, then cooled to 0° C. and quenched with MeOH (5 mL). Sodium borohydride (45 mg, 1.2 mmol) was added. The reaction mixture was stirred for 20 minutes, quenched with 1N HCl (1.5 mL), and stirred for an additional 20 minutes. Next, the solution was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (6×). The organic layers were combined, dried over MgSO4, and concentrated to give the title compound as a yellow oil (83%). 1H NMR (500 MHz, CD3OD) δ ppm 7.83 (s, 1H), 7.46 (d, 1H, J=3.5 Hz), 6.56 (d, 1H, J=3.5 Hz), 4.97 (q, 1H, J=7.0 Hz), 3.83-3.90 (m, 4H), 3.84 (s, 3H), 3.01-3.07 (m, 2H), 2.88-2.94 (m, 2H), 1.54 (d, 3H, J=7.0 Hz); ESI-MS m/z [M+H]+ calc'd for C14H20N4O, 261; found 261.
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