Sodium Carbonate → 5-(3,5-Dichloro-phenyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

Participants

Reaction Steps

To a stirred solution of 500 mg (1.50 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine in 20 ml dioxane under argon at room temperature were added 0.5 ml (1.50 mmol) 3,5-dichlorophenylboronic acid (50% solution in THF/water), 173 mg (0.15 mmol) tetrakis(triphenylphosphine)palladium(O) and 3.0 ml (6.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 1 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed trituration in ether/hexane afforded 328 mg (62%) 5-(3,5-dichloro-phenyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as a beige crystalline solid. ES-MS m/e (%):354 (M{37Cl}+H+, 60), 352 (M{35Cl}+H+, 100).

Provenance & Evidence