Potassium Iodide → HCID 66601835, compound

Participants

Reaction Conditions

Reaction Steps

The reaction was carried out under argon. 4-(Chloromethyl)thiazole hydrochloride (86 mg, 505 μmol; 5.0 eq.), sodium 5-cyano-2-{(4S)-5-cyano-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfinate (150 mg, 101 μmol; purity 32%), potassium carbonate (77 mg, 556 μmol; 5.5 eq.), potassium iodide (84 mg, 505 μmol; 5.0 eq.) and 18-crown-6 (13.4 mg, 51 μmol; 0.5 eq.) were suspended in DMF (3 ml). The mixture was then heated in a closed tube at 110° C. for 15 h. Molecular sieve (4 Å), potassium iodide (84 mg, 505 μmol; 5.0 eq.) and further 4-(chloromethyl)thiazole hydrochloride (86 mg, 505 μmol; 5.0 eq.) were then added, and the reaction mixture was again heated in a closed tube at 100° C. for 2 h. The mixture was then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The title compound was obtained as a solid (37 mg, 66% of theory).

Provenance & Evidence