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Synfacts 2011(3): 0257-0257  
DOI: 10.1055/s-0030-1259504
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

In-Flow Approach to β-Keto Esters and Use in the Synthesis of Pyrimidines

Contributor(s): Victor Snieckus, Toni Rantanen
H. E. Bartrum, D. C. Blakemore, C. J. Moody*, C. J. Hayes*
University of Nottingham and Pfizer Global Research and Development, Sandwich, UK
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

Reported is the synthesis of β-keto esters utilizing an in-flow process and their use, without purification, in reaction with amidine hydrochlorides to produce substituted pyrimidine-4-ols. The in-flow reaction was first optimized in batch form in terms of Lewis acid catalyst and subsequently in the in-flow mode in terms of temperature, flow rate, and back pressure. The resulting keto esters were used directly and transformed into the corresponding pyrimidines in poor to good yields. The substrate scope was well studied.