Editing Pyrimidine (section)

==Occurrence and history==
[[File:PinnerPyrimidin.png|thumb|left|77px|Pinner's 1885 structure for pyrimidine]]
The pyrimidine ring system has wide occurrence in nature<ref name=Lagoja1>{{Cite journal
 | last = Lagoja |first= Irene M.
 | year = 2005
 | title = Pyrimidine as Constituent of Natural Biologically Active Compounds
 | journal = Chemistry and Biodiversity
 | volume = 2
 | issue = 1
 | pages = 1–50
 | url = http://homepage.univie.ac.at/mario.barbatti/papers/pyrazine_pyrimidine/pyrimidine.pdf
 | doi = 10.1002/cbdv.200490173
 | pmid = 17191918
 |s2cid= 9942715
 }}</ref>
as substituted and ring fused compounds and derivatives, including the [[#Nucleotides|nucleotides]] [[cytosine]], [[thymine]] and [[uracil]], [[thiamine]] (vitamin B1) and [[alloxan]]. It is also found in many synthetic compounds such as [[barbiturate]]s and the HIV drug [[zidovudine]]. Although pyrimidine derivatives such as alloxan were known in the early 19th century, a laboratory synthesis of a pyrimidine was not carried out until 1879,<ref name=Lagoja1/> when Grimaux reported the preparation of [[barbituric acid]] from [[urea]] and [[malonic acid]] in the presence of [[phosphorus oxychloride]].<ref name=Grimaux1879>{{Cite journal
 | last = Grimaux | first = E.
 | year = 1879
 | title = Synthèse des dérivés uriques de la série de l'alloxane
 | trans-title = Synthesis of urea derivatives of the alloxan series
 | journal = Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences
 | volume = 88
 | pages = 85–87
 | url = http://visualiseur.bnf.fr/ark:/12148/bpt6k30457/f85.image 
 }} {{free access}}</ref>
The systematic study of pyrimidines began<ref name="ElderfieldVol6">{{cite book |last1=Kenner |first1=G. W. |last2=Todd |first2=Alexander |editor = Elderfield |editor-first=R.C. |title=Heterocyclic Compounds |volume=6 |publisher=Wiley |location=New York |year=1957 |pages=235 }}</ref> in 1884 with [[Adolf Pinner|Pinner]],<ref name=Pinner1884>{{Cite journal
 | author-link = Adolf Pinner
 | last = Pinner | first = A.
 | year = 1884
 | title = Ueber die Einwirkung von Acetessigäther auf die Amidine
 | trans-title = On the effect of acetylacetonate ester on amidines
 | journal = [[Chemische Berichte|Berichte der Deutschen Chemischen Gesellschaft]]
 | volume = A17
 | issue = 2
 | pages = 2519–2520
 | url = http://gallica.bnf.fr/ark:/12148/bpt6k90700r/f942.image|doi=10.1002/cber.188401702173 
 }} {{free access}}</ref>
who synthesized derivatives by condensing [[ethyl acetoacetate]] with [[amidine]]s. Pinner first proposed the name “pyrimidin” in 1885.<ref name=Pinner1885>{{Cite journal
 | author-link = Adolf Pinner
 | last = Pinner | first = A.
 | year = 1885
 | title = Ueber die Einwirkung von Acetessigäther auf die Amidine. Pyrimidin
 | trans-title = On the effect of acetylacetonate ester on amidines. Pyrimidine
 | journal = [[Chemische Berichte|Berichte der Deutschen Chemischen Gesellschaft]]
 | volume = A18
 | pages = 759–760
 | url = http://visualiseur.bnf.fr/ark:/12148/bpt6k90702f/f761.image |doi=10.1002/cber.188501801161 
}} {{free access}}</ref> The parent compound was first prepared by [[Siegmund Gabriel|Gabriel]] and Colman in 1900,<ref name=Gabriel1900>{{Cite journal
 | author-link = Siegmund Gabriel
 | last = Gabriel | first = S.
 | year = 1900
 | title = Pyrimidin aus Barbitursäure
 | trans-title = Pyrimidine from barbituric acid
 | journal = [[Chemische Berichte|Berichte der Deutschen Chemischen Gesellschaft]]
 | volume = A33
 | issue = 3
 | pages = 3666–3668
 | url = http://visualiseur.bnf.fr/ark:/12148/bpt6k90757q/f879.image |doi=10.1002/cber.190003303173 
 }} {{free access}}</ref>
<ref name=Lythgoe1951>{{Cite journal
 | last1 = Lythgoe | first1 = B.
 | last2 = Rayner | first2 = L. S.
 | year = 1951
 | title = Substitution Reactions of Pyrimidine and its 2- and 4-Phenyl Derivatives
 | journal = [[Journal of the Chemical Society]]
 | volume = 1951
 | pages = 2323–2329
 | doi= 10.1039/JR9510002323
 }}</ref>
by conversion of [[barbituric acid]] to 2,4,6-trichloropyrimidine followed by reduction using [[zinc]] dust in hot water.