2,4-Dichloropyrimidine → HCID 57428832, compound

Participants

Reaction Conditions

Reaction Steps

nBuLi (1.9 mL, 1.6 M solution in hexane, 3.0 mmol) was added to a stirred solution of 0.50 mL (3.0 mmol) of 2-(trimethylsilyl)thiophene in 7 mL of THF at −78° C. The solution was stirred for 30 min at −78° C., then warmed to 0° C. and stirred 30 min, before 6.1 mL (3.0 mmol) of a 0.5 M solution of ZnCl2 in THF was added. The reaction solution was stirred for 30 min at 0° C., then transferred via syringe to a microwave vessel containing 315 mg (2.8 mmol) of 2,4-dichloropyrimidine and 158 mg (0.14 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2 mL of THF. The vessel was sealed and heated in a microwave for 10 min at 160° C., then cooled to rt, diluted with 100 mL of Et2O, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography eluting with a linear gradient of 20% EtOAc in hexane to 50% EtOAc to deliver the title compound. MS (M+H)+ 269.

Provenance & Evidence