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

Participants

Reaction Conditions

Reaction Steps

Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) and sealed into a microwave tube. The reaction was heated thermally to 100 °C for 30 minutes 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 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 (66.4 mg, 49.4 %) as an off- white solid.

Provenance & Evidence