CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1.[C:23]([C:25]1[N:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=1)#[CH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:32][O:31][C:29]1[CH:28]=[CH:27][N:26]=[C:25]([C:23]2[CH:24]=[N:14][N:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=23)[N:30]=11-Amino-4-cyanopyridinium 2,4,6-trimethylbenzenesulfonate (Preparation 2, 12.10 g, 37.88 mmol) was added in portions over 6 hours to a stirred suspension of 2-ethynyl-4-methoxypyrimidine (Preparation 1b, 2.54 g, 18.94 mmol) and potassium carbonate (3.93 g, 28.43 mmol) in anhydrous N,N′-dimethylformamide (47 mL) at 0° C. and the resulting mixture was stirred at ambient temperature for 48 hours. The solvent was evaporated and dichloromethane was added to the residue. The solid formed was filtered and the filtrate evaporated to dryness. The crude product was purified by flash chromatography (4:1 hexanes/ethyl acetate) to give the title compound (3.51 g, 74%) as a solid.
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