1,2-Dimethoxyethane → 4-Chloro-6-(2-Methoxyphenyl)pyrimidin-2-Amine

Participants

Reaction Steps

4,6-dichloropyrimidin-2-ylamine (1.0 g, 6.13 mmol) and 2-methoxyphenylboronic acid (0.775 g, 5.1 mmol) were added to a solution of dimethoxyethane (20 mL) and water (3 mL), followed by the addition of NaHCO3 (1.03 g, 12.26 mmol) and (PPh3)2PdCl2 (0.2 g) to this and the reaction mixture was allowed to reflux for 4 h, and then the solvent removed under reduced pressure. The residue was taken up in ethyl acetate (50 mL), and the resulting solution washed with water, dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chropatography on silica gel (eluent CH2Cl2) and recrystallized from hexanes yielding 4-chloro-6-(2-methoxyphenyl)-pyrimidin-2-ylamine (0.76 g; 63%) as light yellow powder.

Provenance & Evidence