2,4-Dichloropyrimidine → HCID 86646783, compound

Participants

Reaction Steps

To a solution of N-(2-methoxy-1-methylethyl)-6-(trimethylstannyl)-4-pyrimidinamine (i.e., the product of Step B) (0.5 g, 1.51 mmol), 2,4-dichloropyrimidine (0.22 g, 1.51 mmol) and copper iodide (12 mg, 0.061 mmol) in N-methylpyrrolidinone (12 mL) under a nitrogen atmosphere was added bis(triphenylphosphine)palladium(II) dichloride (53 mg, 0.076 mmol). The resulting mixture was stirred at reflux for 2 h. After cooling to room temperature, the solution was diluted with water and extracted with diethyl ether 3 times. The organic layers were combined and washed three times with water, then dried and concentrated. The residue was purified on silica gel using a gradient of 100% hexanes to 40% ethyl acetate in hexanes to afford 270 mg of title compound as a solid.

Provenance & Evidence