AskDefine | Define pyrimidines

Extensive Definition

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. It is isomeric with two other forms of diazine.

Nucleotides

three nucleobases found in nucleic acids, namely cytosine, thymine, and uracil, are pyrimidine derivatives:
In DNA and RNA, these bases form hydrogen bonds with their complementary purines. Thus the purines adenine (A) and guanine (G) pair up with the pyrimidines thymine (T) and cytosine (C), respectively.
In RNA, the complement of A is U instead of T and the pairs that form are adenine:uracil and guanine:cytosine.
These hydrogen bonding modes are for classical Watson-Crick base pairing. Other hydrogen bonding modes ("wobble pairings") are available in both DNA and RNA, although the additional 2'-hydroxyl group of RNA expands the configurations through which RNA can form hydrogen bonds.

Chemical properties

A pyrimidine has many properties in common with pyridine, as the number of nitrogen atoms in the ring increases the ring pi electrons become less energetic and electrophilic aromatic substitution gets more difficult while nucleophilic aromatic substitution gets easier. An example of the last reaction type is the displacement of the amino group in 2-aminopyrimidine by chlorine and its reverse. Reduction in resonance stabilization of pyrimidines may lead to addition and ring cleavage reactions rather than substitutions. One such manifestation is observed in the Dimroth rearrangement.
Compared to pyridine, N-alkylation and N-oxidation is more difficult, and pyrimidines are also less basic: The pKa value for protonated pyrimidine is 1.23 compared to 5.30 for pyridine.

Organic synthesis

Pyrimidines can also be prepared in the laboratory by organic synthesis. One method is the classic Biginelli reaction. Many other methods rely on condensation of carbonyls with amines for instance the synthesis of 2-Thio-6-methyluracil from thiourea and ethyl acetoacetate or the synthesis of 4-methylpyrimidine with 4,4-dimethoxy-2-butanone and formamide .
A novel method is by reaction of certain amides with carbonitriles under electrophilic activation of the amide with 2-chloro-pyridine and trifluoromethanesulfonic anhydride :

See also

References

pyrimidines in Bulgarian: Пиримидин
pyrimidines in Catalan: Pirimidina
pyrimidines in Czech: Pyrimidin
pyrimidines in Danish: Pyrimidin
pyrimidines in German: Pyrimidin
pyrimidines in Spanish: Pirimidina
pyrimidines in French: Pyrimidine
pyrimidines in Galician: Pirimidina
pyrimidines in Italian: Pirimidina
pyrimidines in Hebrew: פירימידין
pyrimidines in Lithuanian: Pirimidinas
pyrimidines in Dutch: Pyrimidine
pyrimidines in Japanese: ピリミジン
pyrimidines in Polish: Pirymidyna
pyrimidines in Portuguese: Pirimidina
pyrimidines in Russian: Пиримидин
pyrimidines in Finnish: Pyrimidiini
pyrimidines in Swedish: Pyrimidin
pyrimidines in Ukrainian: Піримідин
pyrimidines in Chinese: 嘧啶
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