HCID 20183381, Verbindung → HCID 20183422, Verbindung
Reaktionsgleichung
[CH3:1][SH:2].CN(C=O)C.Cl[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([CH3:28])[N:21]=[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]=1>O1CCCC1>[CH3:28][C:22]1[N:21]=[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]=[C:18]([C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[S:2][CH3:1])[C:23]=1[C:24]([O:26][CH3:27])=[O:25]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of methyl mercaptan-DMF solution (methylmercaptan 66 g/DMF 306 g) (3.8 ml) and methyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate (1.5 g) in tetrahydrofuran (25 ml) was added and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of water (50 ml) and ethyl acetate (100 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give a residue, which was chromatographed on silicagel eluting with a mixture of n-hexane and ethyl acetate (10:1). The fractions containing the desired product were combined and concentrated in vacuo. The crystalline residue was recrystallized from n-hexane to afford methyl 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (0.2 g).