Water → 3-((5-Bromopyrimidin-2-yl)oxy)quinuclidine

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Reaction Steps

3-Quinuclidinol (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (Aldrich, anhydrous, 10 mL) was treated with potassium tert-butoxide (224 mg, 2 mmol) at ambient temperature for 1 hour. 2-Iodo-5-bromo-pyrimidine (Aldrich, 568 mg, 2 mmol) was then added. After stirring for 30 minutes, the mixture was treated with water (5 mL) and extracted with CHCl3:isopropyl alcohol (10:1, 3×10 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.15) as a solid (287 mg, yield, 50%). 1H NMR (300 MHz, MeOH-d4) δ 1.52-1.65 (m, 1H), 1.66-1.93 (m, 2H), 2.00-2.15 (m, 1H), 2.22-2.31 (m, 1H), 2.79-3.09 (m, 5H), 3.38-3.49 (m, 1H), 5.06-5.15 (m, 1H), 8.64 (s, 2H) ppm. MS (DCl/NH3) m/z 284 (M+H)+ 286 (M+H)+.

Provenance & Evidence