Tetrahydrofuran → HCID 16119575, compound

Participants

Reaction Conditions

Reaction Steps

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (1.0 g, 2.5 mmol), bis(triphenylphosphine)palladium dichloride (290 mg, 0.25 mmol), 1-(trimethylsilyl)-1-propyne (0.44 mL, 3 mmol) and tetrabutyl ammonium fluoride (3 mL, 3 mmol) were added to 20 mL dry THF under nitrogen. The reaction mixture was stirred under nitrogen at 50° C. for 22 hours, then 150 mg of bis(triphenylphosphine)-Palladium dichloride, 0.22 mL of 1-(trimethylsilyl)-1-propyne and 1.5 mL tetrabutyl ammonium fluoride, and 0.1 mL ethanol were added to the reaction mixture. The reaction mixture was stirred under nitrogen for 18 hours at 50° C. The reaction mixture was cooled and poured into saturated aqueous NaHCO4 and extracted into EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on 125 g of flash silica (2%-4% MeOH/CH2Cl2) to give 925 mg of 5-(2-isopropyl-4-methoxy-5-prop-1-ynyl-phenoxy)-pyrimidine-2,4-diamine, MS (M+H)=313.

Provenance & Evidence