Regioselective Synthesis of 3-Aminoimidazo[1,2-a]-pyrimidines under Continuous Flow Conditions

    • Ashlie J. E. Butler
    • Mark J. Thompson
    • Patrick J. Maydom
    • James A. Newby
    • Kai Guo
    • Harry Adams
    • Beining Chen*
    • Department of Chemistry, University of Sheffield, Sheffield, U.K.

    Multicomponent synthesis of 3-aminoimidazo[1,2-a]pyrimidines usually affords a product mixture containing varying amounts of the corresponding 2-amino regioisomer. Modified methods, particularly microwave heating, have been employed to suppress formation of this side-product, but none of the revised protocols are readily amenable to scale. A continuous flow adaptation was found to offer improved regioselectivity toward the targeted 3-amino regioisomer with significantly shorter reaction times and also widened the scope of the reaction to permit the use of aliphatic aldehyde building blocks.

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