反应详情

2-Amino-6-methylpyridine (1.00 g, 9.25 mmol) and acetaldehyde (0.52 mL, 9.34 mmol) were stirred together in anhydrous methyl alcohol for 1 hour at room temperature under a nitrogen atmosphere. The mixture was then treated with sodium triacetoxyborohydride (7.84 g, 37.0 mmol) and five drops of acetic acid and all was allowed to continue stirring for 4 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between water and DCM, and the separated aqueous phase was extracted twice with DCM. The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give a mobile oil which was purified by flash column chromatography, eluting with 2% MeOH/DCM, to give 2-ethylamino-6-methylpyridine (636 mg, 51%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. customThe residue was partitioned between water and DCM
3. extractionthe separated aqueous phase was extracted twice with DCM
4. dry with materialThe combined organics were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a mobile oil which
8. customwas purified by flash column chromatography
9. washeluting with 2% MeOH/DCM