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

Participants

Reaction Conditions

Reaction Steps

tBuLi (2.9 mL, 1.1 M solution in pentane, 3.0 mmol) was added to a stirred solution of 0.52 g (2.8 mmol) of 2-(N-Methyl-N-phenylamino)thiazole in 10 mL of Et2O at −78° C. The solution was stirred for 30 min at −78° C. before 0.59 g (3.0 mmol) of 5-bromo-2-chloropyrimidine and 10 mL of THF were added. The reaction solution was stirred for 30 min at −78° C., and then quenched by the addition of 5 mL of AcOH in 15 mL of MeOH. Solid 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.4 g, 6.1 mmol) was added and the reaction solution was warmed to 0° C. and stirred for 10 min, then poured into 100 mL of a 0.5 M solution of sodium ascorbate, diluted with 300 mL of water and the crude product removed by filtration and washed repeatedly with water. The residue was azeotroped with toluene and purified by flash chromatography eluting with a linear gradient of 10% EtOAc in hexane to 100% EtOAc to deliver the title compound. MS (M+H)+ 383.

Provenance & Evidence