3-Pyridinemethanamine → 2-N-phenyl-4-N-(pyridin-3-ylmethyl)pyridine-2,4-diamine

Temperature

100 °C

Pyridin-3-ylmethanamine (58.1 mg, 0.54 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 flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N2-phenyl-N4-(pyridin-3-ylmethyl)pyridine-2,4-diamine (80 mg, 59.2 %) as an off white solid.

ORD record

ord-4389cfc2af664ae3968b09023440510c

Source dataset

750 AstraZeneca ELN dataset

Original link

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