m-Chloroperbenzoic acid → HCID 178518414, compound

Participants

Reaction Steps

To a 10 mL round bottom flask fitted with a magnetic stirrer bar was added 2-methylthio-4-hydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 11 (40 mg, 0.1 mmol) and 1.0 mL DCM. The reaction flask was cooled in an ice bath and mCPBA (70%, 50mg, 0.22 mmol) was added all at once. After 2 h, two new products were observed by LC. The product eluting at Rt=3.38 min was 2-methylsulfonyl-4-hydroxy-5-(4-chlorophenyl)-6-(2, 4-dichlorophenyl)pyrimidine, m/e=431 (M++1) and that at Rt=2.91 min is 2,4-dihydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: m/e=367 (M+). The mixture was poured into 2 N NaOH and heated briefly. The precipitate that formed was filtered, washed with water and dried under reduced pressure. The title product was recovered. m/e=367 (M+). Rt=2.91 min; 1H-NMR 500 MHz (CDCl3): δ 6.98 (d, J=8 Hz, 2H), 7.08 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 3H), 7.38 (d, J=2 Hz, 1H), 9.8 (bs, 1H), 10.1 (bs 1H).

Provenance & Evidence