[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[CH:10][C:5]2=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:9]=[CH:10][C:5]2=[CH:4][N:3]=1A suspension of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine (100 mg, 0.65 mmol), benzene boronic acid (1.5 eq), copper acetate (2 eq) and pyridine (2 eq) in dichloromethane (2 mL) was heated in the microwave at 80° C. for 15 min. After cooling to rt, the mixture was filtered and the resulting filtrate concentrated to give 6-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine as a green oil (138 mg, 92%) which was used without further purification in the next step.
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