Example 187: Synthesis of 6-(5-bromo-2-chloro-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine. To a stirred solution of copper(II) chloride suspension (1.62 g, 12.0 mmol) and tert-butyl nitrite (15.0 mmol) in acetonitrile (40 ml) was heated to 60°C. Subsequently, an acetonitrile solution (10 ml) of 4-bromo-2-iodoaniline (2.98 g, 10.0 mmol) was added dropwise over 50 min. The reaction mixture was continued to be stirred at 60 °C for 1 hour. After completion of the reaction, the mixture was poured into 20% hydrochloric acid (200 ml) and extracted with ether (2 x 30 ml). The crude product was purified by rapid chromatography on silica gel using hexane as eluent to give 4-bromo-1-chloro-2-iodobenzene (2.4 g, 76% yield).
