[CH3:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][C:5]([C:10]([CH3:12])=[CH2:11])=[C:4]([CH3:13])[N:3]=1.[BH4-].[Na+].Cl>CCO>[CH:10]([C:5]1[CH:6]=[C:7]([CH2:8][NH2:9])[C:2]([CH3:1])=[N:3][C:4]=1[CH3:13])([CH3:12])[CH3:11]To a solution of crude (2,6-dimethyl-5-(prop-1-en-2-yl)pyridin-3-yl)methanamine and 120 mg (0.505 mmol) of CoCl2.6H2O in 5 mL of EtOH at 50° C. was added 115 mg of NaBH4 in 2 portions. After 2 h, 5N HCl was added to a pH=1 and stirring was continued until the bubbling ceased. The mixture was concentrated, and NH4OH was added to pH=9. Some water was added, and the aqueous layer was extracted with the extract of (40 mL CHCl3: 5 mL MeOH: 5 mL H2O). The combined extracts were dried over Na2SO4, filtered, and concentrated to give the crude (5-isopropyl-2,6-dimethylpyridin-3-yl)methanamine which was used without further purification.
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