3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline → (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine

Participants

Reaction Conditions

Reaction Steps

Palladium(II) acetate (6.68 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (10.42 mg, 0.03 mmol) and Cesium carbonate (0.388 g, 1.19 mmol) were put in a 5 mL microwave vial and sealed. The vial was flushed with argon. (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (0.082 g, 0.30 mmol) in DME (5 mL) was added to the vial. The reaction mixture was run in the microwave at 100°C for 60 minutes. Forgot the aniline! Added 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.086 g, 0.36 mmol) and a small spatula of Palladium(II) acetate and 2-(Dicyclohexylphosphino)biphenyl and the reaction mixture was run in the microwave for 60 minutes for 100°C. The reaction mixture was filtrated through celite, concentrated and purified first by preparative chromatography. The productcontaining fractions were pooled, concentrated and partitioned between sat. NaHCO3 (aq) and dichloromethane. The organic layer was washed with sat. NaHCO3 (aq), dried (Na2SO4) and concentrated giving (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine (9.00 mg, 6.84 %).

Provenance & Evidence