Diisopropylamine → 2-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

4-Iodo-2-(methylthio)pyrimidine (39.7 g, 0.157 mol) and diisopropylamine (44.2 mL, 0.315 mol) were dissolved in dry THF (720 mL) and argon gas was bubbled through the solution for 20 min. Copper(I) iodide (2.99 g, 14.3 mmol) and bis(triphenylphosphine)palladium dichloride (5.51 g, 7.85 mmol) were added and then 1-ethynyl-3-nitrobenzene (25.4 g, 0.173 mol) in dry THF (100 mL) was added dropwise over about 30 min with the temperature being maintained at about 25° C. Following complete addition, the mixture was stirred at rt overnight. The mixture is filtered and washed with THF. The filtrate is concentrated under reduced pressure. The residue was washed with EtOAc/MeOH to give pale-yellow solid (42 g).

Provenance & Evidence