Dimethylformamide → HCID 118093617, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, combine tert-butyl N-[[4-(6-chloro-2-methyl-pyrimidin-4-y)oxyphenyl]methylsulfonyl]-N-methyl-carbamate (2.24 g, 3.4 mmol), DMF (2 mL), tetrakis(triphenylphosphine)palladium (1.9 g, 1.7 mmol), and zinc cyanide (2.0 g, 16.8 mmol). Heat the mixture to 90° C. and stir for 3 hours. Quench the reaction with water and sodium hydroxide. Extract the mixture with EtOAc; wash the EtOAc extract(s) with brine; dry over magnesium sulfate; filter and concentrate the filtrate under reduced pressure to provide a residue. Purify the title compound via flash column chromatography using 80 g of silica gel, and eluting with a 0-55% gradient of EtOAc in hexanes. Evaporate the relevant fractions to provide the title compound as a yellow oil (1.2 g, 80.9%). MS (m/z): 419 (M+1).

Provenance & Evidence