[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24](=[O:42])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](C)(C)[O:33][SiH2]C(C)(C)C)=[C:28]([CH3:41])[N:27]=1)([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24](=[O:42])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[C:28]([CH3:41])[N:27]=1)([CH3:22])([CH3:21])[CH3:20]Tetrabutylammonium fluoride (19.6 g, 62.4 mmol) was added to a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (10.5 g, 31.23 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 2.5:77.5) gave (5-hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (6.0 g, 81%).
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