[N:1]([CH2:4][C:5]1[C:6]([CH3:15])=[N:7][C:8]([CH3:14])=[C:9]([C:11]([CH3:13])=[CH2:12])[CH:10]=1)=[N+]=[N-]>CO.[Pd]>[CH3:15][C:6]1[C:5]([CH2:4][NH2:1])=[CH:10][C:9]([C:11]([CH3:13])=[CH2:12])=[C:8]([CH3:14])[N:7]=1A mixture of crude 3-(azidomethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine and 10.2 mg of 10% Pd/C in 6 mL of MeOH was stirred at r.t. under H2 balloon. After 3 h the mixture was filtered through Celite and concentrated to provide (2,6-dimethyl-5-(prop-1-en-2-yl)pyridin-3-yl)methanamine.
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