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

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Reaction Steps

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (10 ml) was treated with potassium tert-butoxide (Aldrich, 224 mg, 2 mmol) at ambient temperature for 1 hour. The mixture was treated with 2-iodo-5-bromo-pyrimidine (TCl, 568 mg, 2 mmol), stirred at room temperature for 1 hour, treated with water (5 mL), and extracted with chloroform:isopropyl alcohol (10:1) (3×20 mL). The extracts were combined and concentrated. The title compound was purified by chromatography (SiO2, CH2Cl2: MeOH: NH3H2O, 90:10:2, Rf. 0.20) as oil (210 mg, yield, 71%). 1H NMR (MeOH-d4, 300 MHz) δ 1.56–1.68 (m, 1H), 1.70–1.90 (m, 2H), 2.05–2.30 (m, 2H), 2.79–3.06 (m, 5H), 3.40–3.48 (m, 1H), 5.11 (m, 1H), 8.64 (s, 2h) ppm. MS (DCl/NH3) m/z 284 (M+H)+, 286 (M+H)+.

Provenance & Evidence