Publication

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

Manfred Schlosser
2004
Journal Articles

Abstract

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)]

Official source

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Manfred Schlosser
2004
Journal Articles

Abstract

Official source

Related concepts (12)

Pyrimidine

Pyrimidine (; pɪˈɹɪ.mɪˌdiːn,_paɪˈɹɪ.mɪˌdiːn) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine (nitrogen atoms at the 1 and 4 positions) and pyridazine (nitrogen atoms at the 1 and 2 positions). In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U).

Pyrimidine dimer

Pyrimidine dimers are molecular lesions formed from thymine or cytosine bases in DNA via photochemical reactions, commonly associated with direct DNA damage. Ultraviolet light (UV; particularly UVC) induces the formation of covalent linkages between consecutive bases along the nucleotide chain in the vicinity of their carbon–carbon double bonds. The photo-coupled dimers are fluorescent. The dimerization reaction can also occur among pyrimidine bases in dsRNA (double-stranded RNA)—uracil or cytosine.

Halogen

The halogens (ˈhælədʒən,ˈheɪ-,-loʊ-,_-ˌdʒɛn) are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group (XVII) or group (VII). The word "halogen" means "salt former" or "salt maker".