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

Participants

Reaction Steps

To a solution of 2-methoxyphenylboronic acid (20.0 g, 155 mmol) in 500 ml of 1,4-dioxane was added 200 ml of saturated aqueous sodium carbonate solution. Argon gas was purged for 30 min at room temperature. 4-Amino-6-chloropyrimidine (28.1 g, 186 mmol) and tetrakistriphenylphosphinepalladium (9.00 g, 77.5 mmol) were added to reaction mixture simultaneously and argon gas was bubbled for another 40 min The reaction mixture was heated to reflux for 16 h, TLC confirms completion of reaction and the mixture was concentrated under reduced pressure. The residue was partitioned between DCM and water. The organic layer was separated, washed with brine, water, dried (Na2SO4) and concentrated. The obtained crude residue purified through silica gel column chromatography eluting with 15% ethyl acetate in DCM to provide 6-(2-methoxyphenyl)pyrimidin-4-amine (18.0 g, 58%). 1H-NMR: (DMSO-d6) δ=8.17 (1H, s), 7.71 (1H, d), 7.41 (1H, t), 6.96-7.06 (2H, m), 6.95 (1H, s), 3.98 (3H, s); MS (m/z)=202.1 (M+H).

Provenance & Evidence