Tetrahydrofuran → HCID 86724352, compound

Participants

Reaction Steps

Into a 25 mL 3-neck RBF equipped with a calcium chloride guard tube, N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)acrylamide (2.0 g), in THF (15 mL), NMO (0.671 g) and OsO4 (4.85 mL 4% in water) solution were charged at room temperature. The reaction mixture was stirred at room temperature for 2 hr. The reaction was monitored on TLC using CHCl3:methanol (9:1). After completion, the reaction mixture was poured in water and extracted into ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure at 40° C. Crude material was purified by Combiflash chromatography eluted with 1.9% methanol in CHCl3 to give 2.0 g of N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)-2,3-dihydroxypropanamide.

Provenance & Evidence