A novel approach to functionalised 5, 7, 8, 9-tetrahydropyrimido [4, 5-b][1, 4] diazepin-6-ones using intramolecular palladium-catalysed amidation

…, PD Johnson, CA Roberts, DA Rudge, I Simpson…

Index: Carr, Gregory R.; Feron, James L.; Johnson, Paul D.; Roberts, Craig A.; Rudge, David A.; Simpson, Iain; Wrigley, Gail L. Tetrahedron Letters, 2012 , vol. 53, # 38 p. 5049 - 5055

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Abstract

The development of a novel palladium-catalysed amidation approach towards 5, 7, 8, 9- tetrahydropyrimido [4, 5-b][1, 4] diazepin-6-one templates is highlighted. The route proceeds through the reaction of an amino amide, generated by 1, 4-addition of an amine to an acrylamide, with 5-bromo-2, 4-dichloropyrimidine and final palladium-catalysed cyclisation to provide the functionalised scaffold in up to 60% isolated yield over three steps. The ...