Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>C(O)C>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1To 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol) in ethanol (EtOH) (10 mL) was added aniline (0.3 mL, 3.3 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto ethyl acetate (EtOAc) and saturated aqueous NaHCO3. The layers were separated and the aqueous layer was further extracted with more EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to provide the crude title compound (620 mg) as a yellow solid. Product contains ˜25% of bis-addition product. LC-MS (ES) m/z=221 [M+H]+.
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