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

Participants

Reaction Steps

The product of Example 18C (150 mg, 0.5 mmol) in ethyl acetate:ethanol (1:1, 5 mL) was treated with fumaric acid (58 mg, 0.5 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (178.2 mg, yield, 98%). 1H NMR (300 MHz, MeOH-d4) δ 1.74-2.11 (m, 3H), 2.20-2.36 (m, 1H), 2.44-2.53 (m, 1H), 3.13-3.40 (m, 5H), 3.68-3.79 (m, 1H), 5.27-5.35 (m, 1H), 6.68 (s, 1.2H), 6.81 (d, J=8.8 Hz, 2H), 7.37 (d, J=8.8 Hz, 2H), 8.74 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+. Anal. Calculated for C17H20N4O.0.57C4H4O4: C, 63.88; H, 6.19; N, 15.54. Found: C, 63.73; H, 6.21; N, 15.51.

Provenance & Evidence