Sodium Iodide → 4-(2-{4-[3-(Thiophen-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenoxy}ethyl)morpholine

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A solution of example 3 (11 mg, 0.038 mmol), cesium carbonate (37 mg, 0.11 mmol), N-(2-chloroethyl)morpholine hydrochloride (7 mg, 0.11 mmol), and sodium iodide (0.013 mmol) in DMF (3 mL) was heated at 60° C. under argon for 16 h. The reaction mixture was then poured into water (25 mL) and washed with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4), concentrated, and purified by flash chromatography [50% Hexanes/CHCl3(NH3)] to give the title compound as a yellow solid [10 mg, 65%, mp =149-151° C., Rf=0.39 (100% CHCl3(NH3))]: 1H NMR (CDCl3) δ8.77 (d, 1H, J=2.2Hz), 8.75 (d, 1H, J=2.2Hz), 8.36 (s, 1H), 7.90 (dd, 1H, J=2.9, 1.3 Hz), 7.69 (dd, 1H, J=4.9, 1.3Hz), 7.52 (d, 2 H, J=8.8Hz), 7.43 (d, 1H, J=4.9, 2.9Hz), 7.06 (d, 2 H, J=8.8Hz), 4.18 (t, 2 H, J=5.7Hz), 3.76 (t, 4 H, J=4.6Hz), 2.85 (t, 2 H, J=5.7 Hz), 2.61 (t, 4 H, J=4.6Hz); FAB MS (M++1) Anal Calcd. for C22H22N4O2S : C, 65.00; H, 5.46; N, 13.78. Found C, 64.98; H, 5.55; N, 14.02.

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