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

Temperature

100 °C

Phenylmethanamine (84 mg, 0.78 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 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 (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 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 preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (85 mg, 63.1 %) as an off-white solid.

ORD record

ord-9f517fc394904161a1e1cc39959a4dbc

Source dataset

750 AstraZeneca ELN dataset

Original link

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