Sodium Carbonate → 6-(2-Methoxyphenyl)pyrimidin-4-amine

Participants

Reaction Steps

To a solution of 2-methoxyphenyl boronic acid (X) (10.3 g, 68.2 mmol) in 300 ml of 1,4-dioxane was added 100 ml of saturated aqueous sodium carbonate solution. Argon gas was purged for 30 min at room temperature. Then 4-amino-6-chloropyrimidine (I) (8.8 g, 68.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.9 g, 3.4 mmol) were added simultaneously and argon gas was bubbled through the mixture for another 20 min. The reaction mixture was heated to reflux for 12 hours (TLC confirmed completion of the reaction) and was then concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. The obtained crude residue was purified by silica gel column chromatography eluting with 15% ethyl acetate in dichloromethane to provide 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (8.0 g).

Provenance & Evidence