Fumaric Acid → 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}aniline hemifumarate

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Reaction Steps

The product of Example 19C (30 mg, 0.1 mmol) in ethyl acetate/ethanol (1:1, 2 mL) was treated with fumaric acid (12 mg, 0.1 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (13.6 mg, yield, 35%). 1H NMR (300 MHz, MeOH-d4) δ 1.84-2.20 (m, 3H), 2.28-2.44 (m, 1H), 2.53-2.62 (m, 1H), 3.16-3.45 (m, 5H), 3.81-3.91 (m, 1H), 5.34-5.42 (m, 1H), 6.68 (s, 1.5H), 6.81 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 8.75 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+. Anal. Calculated for C17H20N4O.0.7C4H4O4O.0.45H2O: C, 61.65; H, 6.19; N, 14.52. Found: C, 61.41; H, 6.02; N, 14.80.

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