Cesium carbonate → HCID 58087958, compound

Participants

Reaction Steps

To (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.093 g, 0.41 mmol) in N,N-dimethylformamide (20 mL) was added Cs2CO3 (0.33 g, 1 mmol)) and 6-isothiocyanato-2′-methoxy-4,5′-bipyrimidine (0.1 g, 0.41 mmol). The suspension was stirred at room temperature for 30 minutes. N,N′-Diisopropylcarbodiimide (0.19 mL, 1.2 mmol) was then added and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated and purified by silica gel chromatography (5-25% [9:1 methanol:ammonium hydroxide]-ethyl acetate) to afford (R)—N-(2′-methoxy-4,5′-bipyrimidin-6-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.072 g, 0.188 mmol, 46% yield) as an off-white solid. 1H NMR (400 MHz, MeOD) δ ppm 9.19 (2 H, s), 8.80 (1 H, d), 7.24 (1 H, br. s.), 4.00-4.09 (4 H, m), 3.76 (1 H, d), 3.23 (1 H, s), 3.08-3.15 (1 H, m), 2.72-3.04 (4 H, m), 1.97-2.22 (2 H, m), 1.38-1.85 (3 H, m). R.T.=1.22; [M+H]+=368.22.

Provenance & Evidence