Cesium carbonate → HCID 59286566, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of dimethyl 6-(pyrazin-2-yl)pyrimidin-4-ylcarbonimidodithioate (0.139 g, 0.501 mmol), Cs2CO3 (0.408 g, 1.253 mmol) and (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.115 g, 0.501 mmol) in N,N-dimethylformamide (10 ml) was heated at 80° C. for 3 h. The mixture was concentrated and purified on silica gel using 0-10% 9.5:0.5 methanol:ammonium hydroxide in ethyl acetate to give (R)—N-(6-(pyrazin-2-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine as an off-white solid (0.066 g, 0.194 mmol, 39%). 1H NMR (400 MHz, MeOD) δ ppm 9.46 (1H, d, J=1.51 Hz), 8.83 (1H, d, J=1.26 Hz), 8.67-8.72 (1H, m), 8.66 (1H, d, J=2.52 Hz), 7.77 (1H, br. s.), 4.05 (1H, d, J=10.32 Hz), 3.75 (1H, d, J=10.32 Hz), 3.18-3.26 (1H, m), 3.04-3.15 (1H, m), 2.87-3.00 (2H, m), 2.70-2.85 (2H, m), 2.04-2.19 (2H, m), 1.54-1.83 (3H, m). MS (LC/MS) R.T.=0.97; [M+H]+=338.29.

Provenance & Evidence