Tetrabutylammonium Fluoride → 4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol

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N-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyridin-2-amine (2.099 g, 5.27 mmol) and tetrabutylammonium fluoride (1M solution in THF, 5.80 ml, 5.80 mmol) were stirred in THF (20 ml) at room temperature for 24 hours until complete. THF was removed in vacuo and the residue partitioned between dichloromethane (75 ml) and sodium bicarbonate (50 ml). The organic layer was washed further with sodium bicarbonate (2×50 ml), then separated and dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on Biotage® silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 90:10:1 by volume) to give the title compound (862 mg, 58%) as a solid. LRMS APCI+ m/z 285 [MH]+.

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