C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]([C:17]([O-:19])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8].[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)=[N:24][C:25]([S:30][CH3:31])=[N:26][C:27]=1C=C)#[N:21].[CH3:41][CH2:42]O>C1(C)C=CC=CC=1.C(Cl)Cl.CCOC(C)=O>[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)=[N:24][C:25]([S:30][CH3:31])=[N:26][C:27]=1[CH2:8][CH2:7][CH:9]([C:17]([O:19][CH2:41][CH3:42])=[O:18])[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])#[N:21]Potassium carbonate (1.88 g) and tert-butyl ethylmalonate were suspended in EtOH (82 ml) and a solution of 5-cyano-2-methylthio-4-(3-nitro-phenyl)-6-vinylpyrimidine (example 27b, 2.71 g) in toluene/CH2Cl2 (33 ml) was slowly added (ca 1.5 h). After the addition was complete, the mixture was stirred for an additional 40 min. The mixture was diluted with EtOAc and washed with water (2×) and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/1 (v/v) as eluent.
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