Benzylamine → 4-N-benzyl-2-N-phenylpyridine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

Phenylmethanamine (144 mg, 1.34 mmol), 4-chloro-N-phenylpyridin-2-amine (250 mg, 1.22 mmol)-diacetoxypalladium (21.94 mg, 0.10 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (81 mg, 0.15 mmol) and sodium 2-methylpropan-2-olate (235 mg, 2.44 mmol) were suspended in DMA (2.50 mL) in a partially sealed tube. The reaction was heated thermally to 80 °C for 1 hour, followed by 90°C overnight and cooled to RT. The reaction mixture was filtered through celite using methanol, neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (33.0 mg, 9.81 %) as a brown gum.

Provenance & Evidence