[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]([C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:5]#[N:6]A mixture of 2-chlorobenzyl cyanide (4.50 g, 0.297 mol), potassium carbonate (6.84 g, 0.0495 mol) and dimethylformamide is stirred 30 minutes at 100° C. and treated dropwise with a solution of 2-chloropyrimidine (2.30 g, 0.0201 mol) in dimethylformamide. The resultant mixture is stirred overnight at 100° C. and treated with additional 2-chlorobenzyl cyanide (1.54 g, 0.0102 mol). The mixture is stirred several more hours at 100° C., cooled and diluted with water. The mixture is extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant brown oil is chromatographed on silica gel with ethyl acetate-hexanes to afford the title compound as a brown oil (3.25 g, 70.8%) which is identified by NMR spectral analysis.
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