2, 6-Diformyl-and 2, 6-diacetylpyridines are readily accessed in good yields (60–90%) via the single-pot reaction of 2, 6-pyridine dicarboxamides with LiAlH4 or MeMgCl in THF at 0– 20° C. The high efficiency of the method illustrates the significance of solubility in the reduction and alkylation of difunctionalized substrates.