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16.12.4.1.4.4.1 Method 1: Reaction of Halopyrimidines with Thiolates

DOI: 10.1055/sos-SD-016-00463

von Angerer, S.Science of Synthesis, (200416520.

Although several examples for the substitution of halogens by alkylthiolates are known[‌561‌,‌567‌,‌654‌,‌668‌,‌672‌,‌673‌] the preferred route of synthesis involves the alkylation of the corresponding pyrimidinethiols. (Arylsulfanyl)pyrimidines, however, are generally prepared by a nucleophilic substitution reaction of the halopyrimidine with the thiophenolate.[‌558‌,‌674‌] The (trifluoromethyl)sulfanyl group can be introduced into the 6-position of tetrafluoropyrimidine by reaction with thiocarbonyl difluoride in the presence of cesium fluoride.[‌675‌] Examples for the substitution of halopyrimidines by metal thiolates are listed in Table 10.

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