Cesium carbonate → HCID 59286597, compound

Participants

Reaction Steps

A suspension of (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (412 mg, 1.800 mmol), dimethyl 6-(4-chloro-1H-imidazol-1-yl)pyrimidin-4-ylcarbonimidodithioate (450 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-chloro-1H-imidazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (265 mg, 48% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.41 (1H, br. s.), 8.60 (1H, d, J=1.01 Hz), 8.25 (1H, d, J=1.51 Hz), 7.44 (1H, d, J=1.51 Hz), 6.78 (1H, s), 4.00 (1H, d, J=9.82 Hz), 3.67 (1H, d, J=9.57 Hz), 3.36 (1H, dd, J=14.86, 1.51 Hz), 2.73-3.06 (5H, m), 2.09-2.22 (2H, m), 1.69-1.79 (1H, m), 1.46-1.64 (2H, m). LCMS: RT=0.54 min, MH+=360.2.

Provenance & Evidence