Cesium carbonate → HCID 59286641, compound

Participants

Reaction Steps

A suspension of (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (412 mg, 1.800 mmol), dimethyl 6-(1H-1,2,4-triazol-1-yl)pyrimidin-4-ylcarbonimidodithioate (400 mg, 1.5 mmol), and cesium carbonate (1222 mg, 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 3% [95:5 MeOH/NH4OH] in CHCl3 to yield (R)—N-(6-(1H-1,2,4-triazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (210 mg, 43% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.45 (1H, br. s.), 9.14 (1H, s), 8.61 (1H, d, J=1.01 Hz), 8.08 (1H, s), 7.39 (1H, s), 4.00 (1H, d, J=9.57 Hz), 3.67 (1H, d, J=9.57 Hz), 3.38 (1H, dd, J=14.86, 1.76 Hz), 2.71-3.08 (5H, m), 2.08-2.23 (2H, m), 1.68-1.80 (1H, m), 1.45-1.64 (2H, m). LCMS: RT=0.46 min, MH+=327.2

Provenance & Evidence