Methyl iodide → Methyl 2-{4-[1-(4-iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropanoate

Participants

Reaction Steps

Lithium diisopropylamide mono (THF) (1.2 equiv. of a 5M solution in cyclohexane) is added to a stirred solution of 5c (1 equiv.) in THF at −78° C. After 15 mins, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1 equiv.) is added followed by iodomethane (1.5 equiv). After 1 h, the reaction mixture is warmed to room temperature and aged until the reaction is deemed complete. The reaction mixture is quenched with saturated aqueous ammonium chloride, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5d.

Provenance & Evidence