Pirimidina: Perbedaan antara revisi

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Baris 139:
 
Pyrimidine is also found in meteorites, but scientists still do not know its origin. Pyrimidine also photolytically decomposes into [[uracil]] under UV light.<ref name="pmid19778279">{{cite journal |author=Nuevo M, Milam SN, Sandford SA, Elsila JE, Dworkin JP |title=Formation of uracil from the ultraviolet photo-irradiation of pyrimidine in pure H<sub>2</sub>O ices |journal=Astrobiology |volume=9 |issue=7 |pages=683–695 |year=2009 |pmid=19778279 |doi=10.1089/ast.2008.0324|bibcode = 2009AsBio...9..683N }}</ref>
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== SynthesisSintesis ==
AsSebagaimana isseringkali oftendijumpai thepada casesistem withheterosiklik parent heterocyclic ring systemsinduk, thesintesis synthesispirimidina oftidak pyrimidinebegitu islazim notdan thatbiasanya commondilakukan anddengan ismenghilangan usuallygugus performedfungsi bydari removing functional groups from derivativesderivatif. Sintesis Primaryprimer synthesesdalam injumlah quantitybesar involvingmelibatkan [[formamideformamida]] have beentelah reporteddilaporkan.<ref name="BrownPyrimidines1994p241">{{cite book |author=Brown, D. J.; Evans, R.F.; Cowden, W. B.; Fenn, M. D. |title=The Pyrimidines |publisher=John Wiley & Sons |location=New York |year=1994 |pages=241–2 |isbn=0-471-50656-7|url= |accessdate=}}</ref>
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As a class, pyrimidines are typically synthesized by the “Principal Synthesis” involving cyclization of beta-dicarbonyl compounds with N-C-N compounds. Reaction of the former with amidines to give 2-substituted pyrimidines, with urea to give 2-pyrimidiones, and guanidines to give 2-aminopyrimidines are typical.<ref name="BrownPyrimidines1994p149">{{cite book |author=Brown, D. J.; Evans, R.F.; Cowden, W. B.; Fenn, M. D. |title=The Pyrimidines |publisher=John Wiley & Sons |location=New York |year=1994 |pages=149–239 |isbn=0-471-50656-7|url= |accessdate=}}</ref>
 
Baris 148:
 
A novel method is by reaction of certain [[amide]]s with [[carbonitrile]]s under electrophilic activation of the amide with 2-chloro-pyridine and [[trifluoromethanesulfonic anhydride]]:<ref>''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}}</ref>
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:[[Image:PyrimidineSynthAmideCarbonitrile.png|400px|PyrimidineSintesis Synthesispirimidina, Movassaghi (2006)]]
 
==Reaksi ==
:[[Image:PyrimidineSynthAmideCarbonitrile.png|400px|Pyrimidine Synthesis Movassaghi 2006]]
Karena menurunnya kadar basa dibandingkan piridina, substitusi elektrofilik pirimidina kurang lancar. [[Protonasi]] atau [[alkilasi]] biasanya berlangsung pada hanya satu atom nitrogen dalam cincin. [[Oksidasi-N]] mono terjadi melalui reaksi dengan perasida.<ref name="JouleMills5thp253">{{cite book | title=Heterocyclic Chemistry |edition=5th |editor1-last=Joule |editor1-first=John A. |editor2-last=Mills |editor2-first=Keith |publisher=Wiley |location=Oxford |year=2010 |pages=253–4 |quote= |isbn=978-1-405-13300-5 |oclc= |doi= |url= |accessdate=}}</ref>
 
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==Reactions==
BecauseSubstitusi-C ofeletrofilik thepirimidina decreasedterjadi basicitypada comparedposisi to pyridine5, electrophilic substitutionyang ofpaling pyrimidinerendah istingkat lesskekurangan facileelektronnya. Nitration, [[Protonationnitrosation]] or, [[alkylationazo coupling]], typicallyhalogenation, takes[[sulfonation]], placeformylation, athydroxymethylation, onlyand oneaminomethylation ofhave thebeen ringobserved nitrogenwith atoms. Mono N-oxidation occurs by reaction withsubstituted peracidspyrimidines.<ref name="JouleMills5thp253BrownPyrimidines1994p9">{{cite book | titleauthor=HeterocyclicBrown, ChemistryD. |edition=5thJ.; |editor1-last=JouleEvans, |editor1-first=JohnR.F.; ACowden, W. |editor2-last=MillsB.; Fenn, M. D. |editor2-firsttitle=KeithThe Pyrimidines |publisher=John Wiley & Sons |location=OxfordNew York |year=20101994 |pages=253–4 |quote=9–13 |isbn=9780-1471-40550656-13300-5 |oclc= |doi= 7|url= |accessdate=}}</ref>
 
Electrophilic C-substitution of pyrimidine occurs at the 5-position, the least electron deficient. Nitration, [[nitrosation]], [[azo coupling]], halogenation, [[sulfonation]], formylation, hydroxymethylation, and aminomethylation have been observed with substituted pyrimidines.<ref name="BrownPyrimidines1994p9">{{cite book |author=Brown, D. J.; Evans, R.F.; Cowden, W. B.; Fenn, M. D. |title=The Pyrimidines |publisher=John Wiley & Sons |location=New York |year=1994 |pages=9–13 |isbn=0-471-50656-7|url= |accessdate=}}</ref>
 
Nucleophilic C-substitution should be facilitated at the 2-, 4-, and 6-positions but there are only a few examples. Amination and hydroxylation has been observed for substituted pyrimidines. Reactions with Grignard or alkyllithium reagents yield 4-alkyl- or 4-aryl pyrimidine after aromatization.<ref name="BrownPyrimidines1994p14">{{cite book |author=Brown, D. J.; Evans, R.F.; Cowden, W. B.; Fenn, M. D. |title=The Pyrimidines |publisher=John Wiley & Sons |location=New York |year=1994 |pages=14–15 |isbn=0-471-50656-7|url= |accessdate=}}</ref>