[CH3:1][CH:2]([CH3:12])[CH2:3][C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=O.C([BH3-])#[N:14].[Na+].C([O-])(=O)C.[NH4+]>CO>[CH3:1][CH:2]([CH3:12])[CH2:3][CH:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[NH2:14]A suspension of 3-methyl-1-(pyridazin-3-yl)butan-1-one (0.85 g, 5.2 mmol; CAN 138835-88-8), sodium cyanoborohydride (1.2 g, 19.2 mmol) and ammonium acetate (1.28 g, 16.6 mmol) in methanol (11.1 mL) was heated at 70° C. for 12 h. The solvent was removed under reduced pressure and the residual oil was partitioned between EtOAc and 1 M aqueous HCl solution. The aqueous layer was basified with 10% aqueous NaOH solution and extracted with EtOAc. The combined extracts were washed with brine and dried over Na2SO4. Filtration and evaporation provided the title compound (233 mg, 27%) as brown oil which was sufficiently pure to be used in the next reaction step. MS (EI): m/e=166.2 [M+H]+.
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