Pyrimidinyl iodides

As illustrated in Schemes 4.1.4 through 4.1.9, the use of pyrimidinyl mercuric acetates have been instrumental in the development of C-nucleosides. Although the comparison in Scheme 4.1.9 illustrates the utility of aryl iodides in addition to aryl mercury compounds, the nature of the specific reagents were quite different. As shown in Scheme 4.1.11, Zhang, etal.,10 utilized pyrimidinyl iodides in the preparation of C-nucleosides from furanose glycals. As illustrated, the product mixture composition was highly susceptible to the specific reaction conditions used. Thus, of the two products shown, either is available in comparable yields. 

A final example illustrating the utility of pyrimidinyl iodides in the preparation of C-nucleosides is shown in Scheme 4.1.12. As shown, Zhang, et al.,11 utilized glycals similar to those incorporated in Scheme 4.1.8. The actual coupling was accomplished utilizing palladium acetate with triphenyl arsine as... 

The nitrogen atom of 3-pyridyl and 5-pyrimidinyl moieties in the N-substituted 8-carboxamide group of 2,3-dimethyl-ll-oxo-ll//-pyrido-[2,l-b]quinazoline-8-carboxamides was quaternized by methyl iodide (88JMC466). 

Acid chlorides are prepared by standard methods and undergo the usual acid chloride reactions. They have found important applications as substrates in the syntheses of ketones by transition metal-catalyzed coupling reactions with organometallics (Section 6.02.5.5.14). Acid chlorides (424) are also good substrates for the preparation of ketones (425) using organomanganese(II) iodide, especially for the preparation of alkyl pyrimidinyl ketones <86ACS(B)764>. 

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