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

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Phenylmethanamine (57.6 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. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (31.5 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 (8.50 mg, 6.32 %) as an off white solid.

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