A suspension of (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (412 mg, 1.80 mmol), dimethyl 6-(4-methyl-1H-imidazol-1-yl)pyrimidin-4-ylcarbonimidodithioate (419 mg, 1.5 mmol), and cesium carbonate (1.22 g, 3.75 mmol) was stirred in DMF (3.8 mL) at 75° C. for 2 h. The reaction was concentrated and purified by flash chromatography on a 40 g silica gel cartridge with a pre-run of 1% [95:5 MeOH/NH4OH] in EtOAc, then 1 to 2% [95:5 MeOH/NH4OH] in CHCl3 to yield (R)—N-(6-(4-methyl-1H-imidazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (472 mg, 92% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.40 (1H, br. s.), 8.56 (1H, d, J=1.01 Hz), 8.28 (1H, d, J=1.26 Hz), 7.21 (1H, s), 6.76 (1H, br. s.), 3.97 (1H, d, J=9.57 Hz), 3.63 (1H, d, J=9.57 Hz), 3.33 (1H, dd, J=14.86, 1.76 Hz), 2.62-3.05 (5H, m), 2.24 (3H, d, J=1.01 Hz), 2.03-2.19 (2H, m), 1.65-1.81 (1H, m), 1.39-1.62 (2H, m). LCMS: RT=0.25, 0.46 min, MH+=340.3.
