Water → HCID 69048427, compound

Participants

Reaction Steps

Potassium carbonate (0.850 g, 6 mmol), water (1 ml) and tetrakis(triphenylphosphine)palladium (0.695 g, 0.6 mmol) were successively added under a nitrogen atmosphere, to a mixture of 4-chloro-2-methanesulfonyl-6-propyl-pyrimidine (1.17 g, 5 mmol) and 3-isopropyl-phenylboronic acid (0.984 g, 6 mmol) in dimethoxyethane (40 mL). The mixture was refluxed for 18 hours then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 7/3) to afford a yellow oil which crystallised in pentane. After filtration, 4-(3-isopropyl-phenyl)-2-methanesulfonyl-6-propyl-pyrimidine (0.380 g) was obtained as an off white solid (mp=82° C.).

Provenance & Evidence