Sodium t-butoxide → N-[3-[[4-(3-cyano-4-pyrrolidin-1-ylphenyl)pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide

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Reaction Conditions

Reaction Steps

5-(2-Chloro-pyrimidin-4-yl)-2-pyrrolidin-1-yl-benzonitrile (40 mg, 0.141 mmol), pyrrolidine-1-carboxylic acid (3-amino-phenyl)-amide (29 mg, 0.141 mmol), Pd2(dba)3 (6.4 mg, 0.007 mmol, 5 mol %), 2-dicyclohexylphosphino-2′-(N,N-dimethylaminobiphenyl) (55.5 mg, 0.141 mmol) and NaOtBu (20.3 mg, 0.211 mmol) were dissolved in 1,4-dioxane (1 mL) and the mixture heated at 100° C. in the microwave (300 W, stirring) for 10 minutes. The mixture was diluted with H2O (10 mL) and EtOAc (30 mL) and the layers separated. The aqueous phase was extracted with EtOAc (20 mL) and the combined organics dried (MgSO4), filtered and the solvent evaporated in vacuo. The mixture was dissolved in DMSO (1.5 mL) and the crude product purified by reversed phase preparative LC-MS. Fractions containing desired product were combined and the solvent evaporated in vacuo. The title compound was afforded as a yellow solid (13.1 mg, 21%); LC-MS, Rt=6.50 min (ANALpH2_MeOH_QC), m/z 453 (MH+).

Provenance & Evidence