4-Toluenesulfonyl chloride → HCID 86667821, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ol (15.0 mg, 0.0368 mmol), tosyl chloride (7.0 mg, 0.0368 mmol) and NEt3 (5.13 μL, 0.037 mmol) in dioxane (2 mL) was heated at 80° C. for 18 hours. Additional portions of tosyl chloride (7.0 mg, 0.037 mmol) and NEt3 (5.1 μL, 0.037 mmol) were added and the mixture continued to heat at 80° C. for 12 hours. The cooled reaction mixture was poured into EtOAc and extracted with 10% HCl. The organic extract was dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography, eluting with 1-2% MeOH/dichloromethane, afforded 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl 4-methylbenzenesulfonate as a brown-yellow film (19.0 mg, 92%). LCMS (APCI+) m/z 562 [M+H]+.

Provenance & Evidence