[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=[N:19]O.N>CO.[Ni]>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:18][NH2:19]A 1 L autoclave was cooled under a stream of nitrogen and charged with 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (14.50 g, 0.052 mol, 1.0 equiv.) and aqueous ammonia (30 mL) in MeOH (300 mL). To this was added Raney Nickel (15.0 g, w/w) and the reaction was stirred at RT under hydrogen (pressure ˜60 psi) overnight. The reaction mixture was then filtered through a Celite® pad and the filtrate was concentrated in vacuo. The crude material was purified by neutral alumina column chromatography using a MeOH/DCM gradient (5 to 10% MeOH to afford (4-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine (97, 8.0 g, 57%) as a brown viscous oily liquid.
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