Toluene → 4-Chloro-6-cyclopropylpyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4,6-dichloropyrimidine (200 mg, 1.342 mmol) in toluene (5.00 mL) in a 2 mL microwave vial was added potassium cyclopropyl(trifluoro)borate (219 mg, 1.477 mmol) (Frontier Scientific Inc.), di(1-adamantyl)-n-butylphosphine (14.44 mg, 0.040 mmol), palladium(II) acetate (6.03 mg, 0.027 mmol) and cesium carbonate (1312 mg, 4.03 mmol) and stirred under argon at 100° C. for 24 hrs in a microwave reactor. The reaction mixture was washed with water (50 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were collected, dried (MgSO4) and evaporated to dryness in vacuo to afford a crude residue. Crude residues were then purified on Biotage Isolera Four (25 g pre-packed cartridge) eluting with 0-15% ethyl acetate-isohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a pale yellow solid (80 mg).

Provenance & Evidence