Ammonia → HCID 69198722, compound

Participants

Reaction Steps

To a 5 mL round bottom flask fitted with a magnetic stir bar and rubber septum was added 1 mL THF and excess ammonia gas. The flask was cooled to 0°. 2-(methylsulfonyl)-4-(3,4-difluorophenoxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Example 20, 270 mg, 0.5 mmol) was added. The reaction mixture was stirred overnight at room temperature. The reaction mixture was washed with saturated NaHCO3, dried over MgSO4, filtered and the solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 60/40 hexanes/ethyl acetate) afforded 2-(amino)-4-(3,4-difluorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/MS: m/e=480 (M+1); Rt=4.2 min; 1H-NMR 500 MHz (CD3OD): δ 6.95 (m, 1H), 7.20 (m, 4H), 7.28 (m, 4H), 7.41 (d, J=2 Hz, 1H).

Provenance & Evidence