Triethylamine → 6-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

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Reaction Steps

To a solution of dichloromethane (15 mL) was added (6-aminopyridin-2-yl)methanol (0.72 g, 5.8 mmol), tert-butyl(chloro)dimethylsilane (1.05 g, 6.95 mmol) and triethylamine (1.05 mL, 7.53 mmol). The mixture was stirred for 24 h and washed with saturated sodium bicarbonate (2×30 mL) and aqueous hydrochloric acid (2×30 mL, 0.1 N). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification was done using silica gel chromatography eluting with hexane: ethyl acetate (1:1) and fractions were combined and concentrated to afford the titled product as a white solid (1.06 g, 70%). HPLC: Rt 2.58 min. (96.5% area). 1H NMR (400 MHz, CDCl3), δ: 7.34 (t, J=7.6 Hz, 1H), 6.75 (d, J=7.6 Hz, 1H), 6.25 (d, J=8.1 Hz, 1H), 4.54 (s, 2H), 4.27 (bs, 2H), 0.84 (s, 9H), 0.11 (s, 6H); LRMS (ESI): m/z: 239.2.

Provenance & Evidence