Sodium Carbonate → HCID 58878056, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(6-chloro-2-methylsulfanyl-pyrimidin-4-yl-amino)-ethanol (404 mg), 3-(trifluoromethyl)phenyl boronic acid (384 mg) and sodium carbonate (585 mg) in toluene (12 ml) with a few drops of DME and ethanol, was added Pd(PPh3)4 (106 mg). The resulting suspension was subjected to microwave heating at 150° C. for 20 mins. Reaction mixture was filtered through a celite pad, washed with ethyl acetate and concentrated in vacuo. The residual brown gum was columned on silica gel using heptane and ethyl acetate (1:1) as eluant. Product obtained was dissolved in tetrahydrofuran and stirred with 3-amino-1,2-propanediol at room temperature for 30 mins then diluted with ethyl acetate (40 ml) and washed with 1M hydrochloric acid (2×100 ml), brine (40 ml), dried over MgSO4 and concentrated in vacuo to give 200 mg of 2-[2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl-amino]-ethanol as a brown gum. Remaining acidic aqueous layer was slowly neutralised and the resulting white precipitate was filtered and dried. This generated 2-[2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-yl-amino]-ethanol as a white solid (450 mg).

Provenance & Evidence