4-(4-Bromobenzyl)morpholine → 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-N-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine

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The aim of the reaction is only optimization and test. The reaction described below was carried out under argon atmosphere. Palladium(II) acetate (2.245 mg, 10.00 µmol) and (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (5.61 mg, 10.00 µmol) were mixed in DME (0.2 mL) in a 1.4 ml vial under argon and stirred for 1 minute at room temperature. The orange pre-mixed Pd-catalyst solution were added to a 10 mL Schlenk-tube containing 4-(4-bromobenzyl)morpholine (0.282 g, 1.1 mmol) and Sodium tert- pentoxide (0.161 g, 1.46 mmol) in DME (1.5 mL). Finally, 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (0.277 g, 1 mmol) was added and the bright orange reaction mixture was stirred at 90 °C. The mixture turned from bright orange into bright yellow in 1 h. The reaction was followed by HPLC. No reaction took place, hence the mixture was discarded.

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