[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[S:13])[NH:8][C:7]([CH3:14])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].I[CH3:24].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([S:13][CH3:24])=[N:8][C:7]([CH3:14])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=16-methoxy-3-methyl-4-phenylisoquinoline-1(2H)-thione (0.9 g) was combined with 20 mL DMF and 0.33 g of NaH (60% dispersion in mineral oil). The reaction was heated to 60 C and stirred for 30 min. Iodomethane (0.33 mL) was added, and the reaction was stirred overnight at 60 C, then poured into saturated aqueous NH4Cl. The mixture was extracted with EtOAc (3×), then the combined organic solutions were washed with water (1×) and brine (1×), dried (Na2SO4) and concentrated to give 6-methoxy-3-methyl-1-(methylthio)-4phenylisoquinoline, which was used directly in the next step.
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