Acetic Acid → HCID 46928995, compound

Participants

Reaction Steps

Under an atmosphere of argon protective gas, 5-cyano-2-{(4S)-5-cyano-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}-N,N-dimethylbenzene sulfonamide (50 mg, 108 μmol) was initially charged in absolute THF (4.5 ml), and a 1 M solution of lithium hexamethyldisilazide (LiHMDS) in THF (130 μl, 130 μmol; 1.2 eq.) was added at −78° C. After 30 min of stirring, iodomethane (77 mg, 542 μmol; 5 eq.) in THF (1 ml) was added, and the mixture was stirred for 16 h with gradual warming from −78° C. to RT. A little acetic acid was then added, and the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative HPLC (column: Gromsil C-18; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave a colorless amorphous solid (7.6 mg, 14% of theory).

Provenance & Evidence