COc1ccccc1CN.Clc1ccnc(Nc2ccccc2)c1>C1CCCC1.CC(=O)N(C)C.CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.[Fe].[Na+].[Pd]>COc1ccccc1CNc1ccnc(Nc2ccccc2)c1
(2-methoxyphenyl)methanamine (73.7 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 and purified by C18 silica chromatography, elution gradient 40 to 70% MeCN in Water + 1% NH4OH. Fractions containing product were evaporated to dryness to afford N4-(2-methoxybenzyl)-N2-phenylpyridine-2,4-diamine (16.00 mg, 10.72 %) as a yellow gum.
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