Cesium carbonate → 4-Chloro-6-phenylpyrimidine

Participants

Reaction Steps

Into a recovery flask equipped with a reflux pipe, 3.35 g of 4,6-dichloropyrimidine, 3.02 g of phenylboronic acid, 1.7 mL of tricyclohexylphosphine (abbreviation: PCy3), 14.7 g of cesium carbonate, 0.31 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3), and 30 mL of dioxane were put, and the air in the flask was replaced by argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent of this reaction solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and hexane as a developing solvent in a volume ratio of 1:1, to give 4-chloro-6-phenylpyrimidine (light yellow powder, 34% in yield). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 1 is shown by (a-1).

Provenance & Evidence