Benzene, 1-iodo-3-(trifluoromethyl)- → 5-bromo-4-methoxy-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine

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_EN06995-11\Reaction_ and many others **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.215 ml, 1.49 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.254 g, 1.24 mmol), PALLADIUM(II) ACETATE (0.014 g, 0.06 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.054 g, 0.09 mmol) and cesium carbonate (0.487 g, 1.49 mmol) were mixed in toluene (5ml), purged with nitrogen and stirred in a sealed tube at 80 °C overnight. LCMS: pH = 3, 2 minute run time, Rt = 0.66 min (32% by UV), m/z: 204 (MH+) \- 316 (M-H-) - ?; Rt = 1.10 min (15% by UV), m/z: 257, 306 (MH+) - 316 (M-H-) - ?; Rt = 1.28 min (25% by UV), m/z: 350, (MH+) product ?. The reaction mixture was diluted with EtOAc (20 ml), filtered through a celite pad and concentrated to give 902 mg yellow oil. TLC (1:1 - EtOAc : n-heptane) see diagram UV only This was disolved in DCM, absorbed onto a samplet and purified on a 10 g Biotage SNAP column (approx column volume = 7 ml), eluting with a step-wise gradient from 0 : 10 to 4 : 6 EtOAc : n-heptane using a Thomson pump collecting 12 ml fractions. F1 - y = 38 mg - GCMS and NMR - show it to be product F2 - y = 229 mg \- GCMS and NMR - show it to be bromo SM **_Conclusion:_ \- ** Abandoned - to be repeated with xanphos

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