Pyrimidine



Pyrimidine
IUPAC name pyrimidine
Identifiers
CAS number 289-95-2
PubChem 9260
MeSH pyrimidine
SMILES C1=CN=CN=C1
Properties
Molecular formula C4H4N2
Molar mass 80.088
Melting point

20–22 °C

Boiling point

123–124 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Pyrimidine is a diazine.

Nucleotides

Three thymine, and uracil, are pyrimidine derivatives:



In guanine (G) - pair up with the pyrimidines thymine (T) and cytosine (C) respectively.

In cytosine.

These hydrogen bonding modes are for classical Watson-Crick base pairing. Other hydrogen bonding modes ("wobble pairings") are available in both RNA expands the configurations through which RNA can form hydrogen bonds.[citation needed]

Chemical properties

A pyrimidine has many properties in common with amino group in 2-aminopyrimidine by chlorine[2] and its reverse.[3] 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.[citation needed]

Compared to pyridine pKa value for protonated pyrimidine is 1.23 compared to 5.30 for pyridine.[citation needed]

Organic synthesis

Pyrimidines can also be prepared in the laboratory by formamide [5].

A novel method is by reaction of certain trifluoromethanesulfonic anhydride [6]:

See also

References

  1. ^ Heterocyclic Chemistry (3rd Edition) Thomas. L. Gilchrist ISBN 0-582-27843-0
  2. ^ Organic Syntheses, Coll. Vol. 4, p.182 (1963); Vol. 35, p.34 (1955) Link
  3. ^ Organic Syntheses, Coll. Vol. 4, p.336 (1963); Vol. 35, p.58 (1955) Link
  4. ^ Organic Syntheses, Coll. Vol. 4, p.638 (1963); Vol. 35, p.80 (1955) Link
  5. ^ Organic Syntheses, Coll. Vol. 5, p.794 (1973); Vol. 43, p.77 (1963) Link
  6. ^ Single-Step Synthesis of Pyrimidine Derivatives Mohammad Movassaghi and Matthew D. Hill J. Am. Chem. Soc.; 2006; 128(44) pp 14254 - 14255; (Communication) doi:10.1021/ja066405m


Nucleobases: Cytosine)
Nucleosides: Thymidine | Cytidine/Deoxycytidine
Nucleotides: monophosphates (cADPR)
Deoxynucleotides: monophosphates (dAMP, dGDP, TDP, dCDP) | triphosphates (dATP, dGTP, TTP, dCTP)
Ribonucleic acids: snoRNA
Deoxyribonucleic acids: mtDNA
Nucleic acid analogues: morpholino
Cloning vectors: phagemid | plasmid | lambda phage | cosmid | P1 phage | fosmid | BAC | YAC | HAC
 
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