Cesium carbonate → HCID 52920235, compound

Participants

Reaction Steps

A suspension of (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (135 mg, 0.59 mmol), dimethyl 6-(1H-pyrazol-1-yl)pyrimidin-4-ylcarbonimidodithioate (130 mg, 0.49 mmol), and cesium carbonate (399 mg, 1.23 mmol) was stirred in DMF (1.2 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 isocratic 1% [95:5 MeOH/NH4OH] in CHCl3 to yield (R)—N-(6-(1H-pyrazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (105 mg, 66% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.46 (1H, br. s.), 8.58 (1H, d, J=1.01 Hz), 8.50 (1H, dd, J=2.64, 0.63 Hz), 7.74 (1H, d, J=1.01 Hz), 7.47 (1H, br. s.), 6.44 (1H, dd, J=2.64, 1.64 Hz), 3.98 (1H, d, J=9.57 Hz), 3.65 (1H, d, J=9.57 Hz), 3.39 (1H, dd, J=14.86, 1.51 Hz), 2.71-3.09 (5H, m), 2.10-2.26 (2H, m), 1.69-1.80 (1H, m), 1.48-1.64 (2H, m). LCMS: RT=0.51 min, MH+=326.2.

Provenance & Evidence