Benzylamine → 4-N-benzyl-2-N-(4-methoxyphenyl)pyridine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

Phenylmethanamine (50.2 mg, 0.47 mmol), 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (100 mg, 0.43 mmol) and sodium 2-methylpropan-2-olate (82 mg, 0.85 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (28.4 mg, 0.05 mmol) and diacetoxypalladium (7.65 mg, 0.03 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-(4-methoxyphenyl)pyridine-2,4-diamine (77 mg, 59.2 %) as an off-white solid.

Provenance & Evidence