2-Chloro-6-methylaniline → HCID 67389359, compound

Participants

Reaction Steps

To a solution of 4-(2-chloro-4-pyrimidinyl)-N-(tetrahydro-2H-pyran-4-yl)-1,3,5-triazin-2-amine (i.e., the product of Step A) (125 mg, 0.42 mmol) in toluene (4.0 mL) under nitrogen was added 2-chloro-6-methylaniline (180 mg, 1.27 mmol), cesium carbonate (273 mg, 0.84 mmol), tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol), and ((±)-BINAP) (28 mg, 0.044 mmol), and the resulting mixture was stirred and heated at reflux for 6 h. After cooling to room temperature, the mixture was concentrated and purified using column chromatography on silica gel eluted with 40% acetone in hexanes to give 57 mg of the title compound as a yellow solid.

Provenance & Evidence