CC[C@H]1CNC(=O)O1.Cc1nc(/N=C/N(C)C)nc(Cl)c1Cc1ccc(CC#N)cc1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[K+].[K+].[Pd]>CC[C@H]1CN(c2nc(/N=C/N(C)C)nc(C)c2Cc2ccc(CC#N)cc2)C(=O)O1Palladium(II) acetate (8.22 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes.(E)-N'-(4-chloro-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (240 mg, 0.73 mmol), (S)-5-ethyloxazolidin-2-one (169 mg, 1.46 mmol) and POTASSIUM CARBONATE (202 mg, 1.46 mmol) were added and the mixture was heated at 100 °C for 1 hour. The solvent was evaporated under reduced pressure and the crude product was purified by flash silica chromatography, elution gradient 2 to 5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford (S,E)-N'-(5-(4-(cyanomethyl)benzyl)-4-(5-ethyl-2-oxooxazolidin-3-yl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (136 mg, 45.7 %) as a colorless solid.
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