2-Acetylamino-4-aminotoluene → N-[5-({3-Cyano-7-[(1-Methyl-1h-Imidazol-4-Yl)amino]pyrazolo[1,5-A]pyrimidin-5-Yl}amino)-2-Methylphenyl]acetamide

Temperature

100 °C

To a microwave vial containing N-(5-amino-2-methylphenyl)acetamide (0.096 g, 0.58 mmol), 5-chloro-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.08 g, 0.29 mmol), sodium tert-butoxide (0.093 g, 0.96 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.014 g, 0.03 mmol) was added DMA (1.8 ml). Vial was flushed with argon and to it was added Pd2(dba)3 (0.013 g, 0.01 mmol) and the reaction was heated in a MW reactor at 100 C for 50 min . Reaction was filtered through celite and the filterate diluted with EtOAC (5 ml) and the organic solution was washed with minimum amt of brine( 1X 5 ml) and organic layer dried over Na2SO4 filtered and concentrated to give crude liquid. this was purified by flash column using 5-8% MeOH: DCM (1% NH4OH) as gradient to give N-(5-(3-cyano-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-methylphenyl)acetamide (0.015 g, 12.78 %) as desired product. nmr & MASS AGREE WITH THE STRUCTURE.

ORD record

ord-a0aa244ac0f34a23886d9e4b9c227fa6

Source dataset

750 AstraZeneca ELN dataset

Original link

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