Cesium carbonate → 4-[4-(4-Iodo-2,6-dimethylphenoxy)pyrimidin-2-ylamino]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-chloro-pyrimidin-2-ylamino)benzonitrile (Ludovici, et al. ibid) 2 (600.0 mg, 2.60 mmol), 4-iodo-2,6-dimethylphenol (Chabrier, et al., Ibid) (838.0 mg, 3.38 mmol) and cesium carbonate (2.20 g, 6.76 mmol) in dry DMF (12 mL) was heated to 90° C. (Zhang, et al., Tetrahedron Lett., 2002, 43, 8235-8239). After 3 hours, TLC (EtOAc/hexane=50:50) revealed a more polar product and consumption of compound 2. The mixture was poured into water (100 mL) and the product extracted into EtOAc (3×50 mL). The combined extracts were washed with brine (50 mL) followed by water (2×50 mL), and then dried over (Na2SO4) and the solvent evaporated in vacuo to furnish a residue that was subjected to silica-gel column chromatography using EtOAc/hexane (50:50) as eluent to produce 3 as a white solid (982.0 mg, 2.22 mmol, 85%).

Provenance & Evidence