Methyl iodide → HCID 58133738, compound

Participants

Reaction Steps

The reaction was carried out under argon. Allyl (4S)-4-[4-cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (260 mg, 0.5 mmol) was initially charged in absolute THF (10 ml), and a 1 M solution of lithium hexamethyldisilazide (LiHMDS) in THF (0.6 ml, 600 μmol; 1.2 eq.) was added at −78° C. After 20 min of stirring, iodomethane (355 mg, 2.5 mmol; 5 eq.) was added, and the mixture was stirred for 16 h with gradual warming from −78° C. to RT. The reaction mixture was then concentrated under reduced pressure, and the residue was subjected to flash chromatography on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 55:45). The title compound was obtained as a colorless solid (157 mg, 59% of theory).

Provenance & Evidence