Regioselective 2-Amination of Polychloropyrimidines.

doi:10.1021/acs.orglett.6b00799

Paper

Regioselective 2-Amination of Polychloropyrimidines.

Published Apr 15, 2016 · Sean M. Smith, S. Buchwald

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Abstract

The regioselective amination of substituted di- and trichloropyrimidines affording the 2-substituted products is reported. While aryl- and heteroarylamines require the use of a dialkylbiarylphosphine-derived palladium catalyst for high efficiency, more nucleophilic dialkylamines produce 2-aminopyrimidines under noncatalyzed SNAr conditions. The key is the use of 5-trimethylsilyl-2,4-dichloropyrimidine as a surrogate for the parent dichloropyrimidine. For more challenging cases, the 2-chloro-4-thiomethoxy analogues were prepared and exclusively afford the desired 2-aminated-4-thiomethoxypyrimidine products.

Study Snapshot

Regioselective 2-amination of polychloropyrimidines can be achieved using 5-trimethylsilyl-2,4-dichloropyrimidine as a surrogate, or by using 2-chloro-4-thiomethoxy analogues for more challenging cases.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Regioselective 2-Amination of Polychloropyrimidines.

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References

Transition metal-catalyzed C-C bond formation via C-S bond cleavage: an overview.

Transition metal-catalyzed C-C bond formation via C-S bond cleavage offers a promising alternative to organo-halide reagents for the synthesis of interesting organic compounds.

Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

Palladium precatalysts with electron-rich di-tert-butylphosphino biaryl ligands enable the use of bulky ligands in palladium-catalyzed cross-coupling reactions and various C-N and C-O bond-forming

Transition-metal mediated carbon-sulfur bond activation and transformations.

Transition metal compounds show promise for deep hydrodesulfurization of petroleum feedstocks and offer potential for useful synthetic protocols in cross-couplings and biomimetic organic synthesis.

Synthesis of 4,6-disubstituted 2-(4-morpholinyl)pyrimidines by cross-coupling reactions using triorganoindium compounds.

This study demonstrates an efficient and versatile method for synthesizing 4,6-disubstituted 2-(4-morpholinyl)pyrimidines using triorganoindium compounds, enabling the synthesis of various non-symmetrical pyrimidines with potential bioactive properties.

Hybrid Heterocycle-Containing Electron-Transport Materials Synthesized by Regioselective Suzuki Cross-Coupling Reactions for Highly Efficient Phosphorescent OLEDs with Unprecedented Low Operating Voltage

Hybrid heterocycle-containing electron-transport materials synthesized by regioselective Suzuki cross-coupling reactions enable efficient phosphorescent OLEDs with unprecedented low operating voltages.

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