[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[H-].[Na+].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1>CN(C=O)C>[Cl:12][C:13]1[N:18]=[C:17]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[N:2]2)[C:16]([Cl:20])=[CH:15][N:14]=1A solution of benzotriazole (2.14 g, 18.03 mmol) in DMF (10 mL) was slowly added at 0° C. to a solution of NaH (60% in mineral oil, 0.850 g, 21.3 mmol) in DMF (20 mL) under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 15 minutes; a solution of 2,4,5-trichloropyrimidine (3 g, 16.39 mmol) in DMF (20 mL) was then slowly added at 0° C. The reaction mixture was allowed to reach RT while stirring overnight. The solvent was evaporated under reduced pressure; the residue was taken up with EtOAc and washed 3× with water. The aqueous layers were combined and extracted 3 times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give a crude oil. This material was purified via flash chromatography (heptane/EtOAc, 8/2) to give 1.5 g (34% yield) of 1-(2,5-dichloro-pyrimidin-4-yl)-1H-benzotriazole.
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