Stannylation reaction and cross-couplings in pyrimidines
摘要：
Pyrimidines have been stannylated in the activated 4-position by thermal decar☐ylation of the corresponding car☐ylic organotin esters. The decar☐ylation can be catalyzed by bis(acetonitrile)palladium(II) dichloride. 4-Iodopyrimidines are 4-stannylated either by substitution reactions with tri- n-butyltin-copper or by coupling reaction with hexamethyl- or hexa-n-butyl-ditin and Pd(II) catalysis. The stannylated pyrimidines form new carbon-carbon bonds by Pd(II)-catalyzed cross-couplings, tert-Butyldimethylsilyl-, dimethylthexylsilyl- and tert-butyldiphenylsilyl-oxymethyl (tri- n-butyl)tin have been synthesized and used in Pd(II)-catalyzed cross-coupling reactions with 4-chloropyrimidines. The silyi groups were not cleaved off during exposure to fluoride ions in aqueous media but were readily removed by fluoride ions in THF to yield the 4-hydroxymethylpyrimidine.
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DOI：
10.1016/0040-4020(89)80011-0
被引量：
年份：
1989
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