Brominated 4-(trifluoromethyl)pyrimidines: A convenient access to versatile intermediates

An expedient route to all three monobrominated and all three dibrominated isomers of 4-(trifluoromethyl)pyrimidine, and to several other halogenated pyrimidines, is described. Key steps are the electrophilic introduction of the halogen in the 5-position of 2- or 4-pyrimidinones, the bromodeoxygenation of pyrimidinones or thiopyrimidinones using phosphorus tribromide, and the partial debromination of dibromo-4-(trifluoromethyl)pyrimidines. [on SciFinder (R)]

Published in:
European Journal of Organic Chemistry, 17, 3714-3718
CAN 141:395506 28-16 Heterocyclic Compounds (More Than One Hetero Atom) Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 57-13-6 (Urea); 62-56-6 (Thiourea); 372-31-6 (Ethyl 4,4,4-trifluoroacetoacetate); 326894-81-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of halogenated 4-(trifluoromethyl)pyrimidines); 368-54-7P; 672-45-7P; 1546-78-7P; 104048-92-2P; 126538-81-6P; 785777-90-4P; 785777-94-8P; 785777-95-9P; 785777-96-0P; 785777-97-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of halogenated 4-(trifluoromethyl)pyrimidines); 785777-87-9P; 785777-88-0P; 785777-89-1P; 785777-91-5P; 785777-92-6P; 785777-93-7P; 785777-98-2P; 785777-99-3P; 785778-00-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of halogenated 4-(trifluoromethyl)pyrimidines)
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 Record created 2006-03-03, last modified 2018-01-27

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