Potassium Hydroxide → HCID 86732440, compound

Participants

Reaction Conditions

Reaction Steps

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol (3-1, 0.211 mmol, 1. eq.) were suspended in 843 μl of 30% aq. potassium hydroxide solution (5.72 mmol, 27 eq.) and 843 μl of acetonitrile. The suspension was cooled with a freezing mixture to −75° C. 93 μl of 2-chloro-2,2-difluoro-1-phenylethanone (0.632 mmol, 3 eq.) were added dropwise. The freezing mixture was removed. The reaction mixture was stirred at 80° C. bath temperature for 4 hours. Then the mixture was partitioned between water and dichloromethane/isopropanol 4:1. The phases were separated and the aqueous layer was extracted twice with dichloromethane/isopropanol 4:1. The combined organic layers were washed with brine, dried over a silicone filter and concentrated in vacuo. Preparative HPLC purification provided 4 mg (0.01 mmol, 3.2%) of the analytically pure target compound.

Provenance & Evidence