Acetic Acid → 4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-amine

Participants

Reaction Steps

tert-Butyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-ylcarbamate (0.352 g, 0.96 mmol) was dissolved in 2 mL CH2Cl2. tert-Butyl (dimethyl)silyl trifluoromethanesulfonate was added and the solution was stirred for 5.5 hours. N-Ethyl-N,N-diisopropylamine (0.669 mL, 3.84 mmol) was added and the solution was stirred for 0.5 hour. Saturated NaHCO3 (aq) was added and the precipitate was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford a yellow oil. The oil was dissolved in 10 mL MeOH. Acetic acid (0.20 mL) was added and the solution was stirred for 0.5 hour. The reaction was concentrated in vacuo to afford an off white solid. The solid was purified by flash column chromatography (1:1 EtOAc/hexanes). The fractions containing the desired compound were concentrated to dryness to afford 12-1 as a colorless oil. 1H NMR (CDCl3) δ 6.54 (s, 1H), 6.46 (s, 1H), 5.87 (bs, 2H), 4.65 (s, 2H), 2.73 (q, 2H, J=7.63 Hz), 1.29 (t, 3H, J=7.63 Hz), 0.95 (s, 9H), 0.12 (s, 6H).

Provenance & Evidence