Cesium carbonate → HCID 67282035, compound

Participants

Reaction Conditions

Reaction Steps

((1R,2S)-2-(3-fluorophenyl)-2-((tosyloxy)methyl)cyclopropyl)methyl acetate (8, 11.05 g, 0.028 mol, 1.0 equiv.), 2,4-dimethylpyrimidin-5-ol (3.74 g, 0.030 mol, 1.07 equiv.), and cesium carbonate (22.94 g, 1.8 equiv.) were dissolved in ACN (110.5 mL), under nitrogen. The solution was stirred vigorously and heated to 65-70° C. for 2-3 hours. The reaction was monitored by HPLC and TLC (EtOAc/Heptane=1/1). Once complete, aqueous 1 N NaOH solution (71.82 mL) was added to the reaction mixture. The reaction mixture was stirred at 20-25° C. for 10-16 h, and was monitored by HPLC and TLC (EtOAc/Heptane=1/1). Once the hydrolysis reaction was complete, the reaction mixture was diluted with MTBE (110.50 mL) and stirred for at least 15 min. The aqueous layer was back extracted once with MTBE (55.25 mL). The organic layers were combined and washed once with saturated aqueous NaCl solution (33.15 mL), The solvent was removed under reduced pressure to afford the title compound; ((1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-(3-fluorophenyl)cyclopropyl)methanol: (11, 8.51 g).

Provenance & Evidence