Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH2:18]Cl)=[CH:13][CH:12]=1.CO.O.C(O)(C)C.[K+].[Br-]>CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH2:18][N:5]2[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]2=[O:9])=[CH:13][CH:12]=1
The title compound was prepared from 5-chloropyrimidin-2-one hydrochloride (10 mmol) and 4-fluoro-1(chloromethylthio)benzene (10 mmol) in a manner similar to that described in Example 2. The reaction time was 21/2h. Yield: 1.60 g (59%) of the N- and O-isomers in the ratio 2:1. The N-isomer was isolated by its lower solubility in methanol; m.p. 179° C. (MeOH/H2O/isoPrOH). 1H NMR (DMSO/d6): δ 5.25 (CH2), 6.9-7.7 (Ph), 8.07 and 8.53 (H-4 and H-6, J 4 Hz). IR (KBr): 1660 cm-1 (CO). (Found: C49.80; H2.54. Calc. for C11H8ClFN2OS: C48.81; H2.98). MS [70 eV, m/z (% rel. int.]): 270/272 (4/2,M), 143/145 (100/32).
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