2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(2-Chloro-5-fluoropyrimidin-4-yl)-N-methyl-N-phenylthiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A 1.6 M solution of tBuLi in heptane (1.6 mL, 2.6 mmol) was added to a stirred solution of 0.44 g (2.3 mmol) of 2-(N-Methyl-N-phenylamino)thiazole in 8 mL of THF at −78° C. The solution was stirred for 15 min at −78° C. before 0.24 mL (2.6 mmol) of 2-chloro-5-fluoropyrimidine and 2 mL of THF were added. The reaction solution was stirred for 10 min at −78° C., then quenched by addition of 1 mL of AcOH in 1 mL of MeOH. Solid 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.1 g, 4.6 mmol) was added and the reaction solution was warmed to 0° C. and stirred for 30 min, poured into 50 mL of a 0.5 M solution of sodium ascorbate, diluted with 200 mL of water and the crude product removed by filtration and washed repeatedly with water. The residue was dried by toluene co-evaporation to deliver the title compound. MS (M+H)+ 321.

Provenance & Evidence