1,2-Dimethoxyethane → 4-Chloro-6-(2-methoxyphenyl)pyrimidine

Participants

Reaction Steps

To a solution of 4,6-dichloropyrimidine (6.0 g, 40 mmol) and 2-methoxyphenylboronic acid (4.41 g, 29 mmol) in mixture of dimethoxyethane (120 mL) and water (18 mL) were added NaHCO3 (6.72 g, 80 mmol) and (PPh3)2PdCl2 (0.84 g) and the reaction mixture was refluxed for 8 h, and concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (100 mL) and the solution washed with water, dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The obtained crude product was purified by flash chropatography on silica (eluent CH2Cl2) and recrystallized from hexanes. Yield of 4-chloro-6-(2-ethoxyphenyl)-pyrimidine 4.78 g (75%).

Provenance & Evidence