Cesium carbonate → HCID 59286574, compound

Participants

Reaction Steps

To suspension of (S)-1-(6-(2-fluoropyridin-3-yl)pyrimidin-4-yl)-3-((3-hydroxyquinuclidin-3-yl)methyl)thiourea (0.2 g, 0.515 mmol) in N,N-dimethylformamide (20 mL) was added Cs2CO3 (0.168 g, 0.515 mmol) and DIC (0.241 mL, 1.545 mmol). The suspension was stirred at room temperature for 18 h, then at 60° C. for 3 h. The mixture was concentrated and the residue was purified on silica gel using 2-7% 9.5:0.5 methanol:ammonium hydroxide in ethyl acetate to afford (R)—N-(6-(2-fluoropyridin-3-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine as a pale yellow solid (0.029 g, 0.081 mmol, 16%). 1H NMR (400 MHz, MeOD) δ ppm 8.83 (1H, d, J=1.26 Hz), 8.55 (1H, ddd, J=9.76, 7.62, 2.01 Hz), 8.29 (1H, dt, J=3.02, 1.51 Hz), 7.46 (1H, ddd, J=7.37, 5.10, 1.89 Hz), 7.33 (1H, s), 4.06 (1H, d, J=10.32 Hz), 3.76 (1H, d, J=10.32 Hz), 3.25 (1H, s), 3.09-3.19 (1H, m), 2.95 (2H, t, J=7.68 Hz), 2.74-2.91 (2H, m), 2.04-2.26 (2H, m), 1.55-1.87 (3H, m). MS (LC/MS) R.T.=1.24; [M+H]+=355.28.

Provenance & Evidence