m-Chloroperbenzoic acid → HCID 178437724, compound

Reaction equation

[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([CH:19]([S:21][CH3:22])[CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>ClC(Cl)C.ClCCl>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([CH:19]([S:21]([CH3:22])=[O:31])[CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:2])([CH3:4])[CH3:3]

Participants

Procedure

10.25 g (30 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-methylthioethyl)pyrimidine were placed in 120 ml of dichloroethane, and a solution of 7.40 g (30 mmol) of 70% 3-chloroperbenzoic acid in 50 ml of dichloromethane was added dropwise at 0° C. The mixture was stirred at room temperature for 8 hours and extracted by stirring with sodium bicarbonate solution and water. The organic phase was dried and concentrated, to give 10.5 g (98% of theory) of a colorless resin (diastereomer mixture).