DE1695373C - 2 (Di n propylacetamido ^ pyrimidine and process for its preparation - Google Patents
2 (Di n propylacetamido ^ pyrimidine and process for its preparationInfo
- Publication number
- DE1695373C DE1695373C DE1695373C DE 1695373 C DE1695373 C DE 1695373C DE 1695373 C DE1695373 C DE 1695373C
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidine
- propylacetamido
- preparation
- pyridine
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 propylacetamido Chemical group 0.000 title description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Description
1 «953731 «95373
Das !-(Di-n-propylacetamidoJ-pyrinudJn der FormelDas! - (Di-n-propylacetamidoJ-pyrinudJn der formula
C3H,C 3 H,
hat als Arzneimittel überlegene beruhigende, Eigen» schäften; es kann jedoch auch für die Hersteilung, gewisser Proteine sowie als Strahlenschutzmittel dienen.as a medicinal product has superior calming, properties » stocks; However, it can also be used for the production, certain proteins as well as radiation protection agents serve.
Das 2-iDi»n*pTopyl3cetamido)-pyr!niidin wird hergestellt, indem nass 2*Aminopyr»ntdin mit Dipropy!- (Cisig-siiurcchiond ohne Anwendung: von Lösungsmitteln oder in Gegenwart von Pyridin bei einer Temperatur von tß Itm WC reagieren JäßLThe 2-IDI "n * pTopyl3cetamido) pyr niidin is prepared by wet 2 * Aminopyr" ntdin with dipropylene - (Cisig-siiurcchiond without Application:! Respond solvents or in the presence of pyridine at a temperature of TSS Itm toilet JäßL
Wird d« Umsetzung ohne Pyiidin duichtcfiihrt, |»t es zwecliffSßsft mt Bindung des Chlorwasserstoffs tincn Überschuß vun t Mol ^-Aüilnopyrimidin anzU' wenden, ^^iwi e* genügt. Use miteinander gemischten t SluraJe fang auf U) bis ?Ö"C zs er· Pte KriktioßiRiiiife wird dann aJkalheh mit wöfei als liUseIf the reaction is carried out without pyiidine, it is sufficient to use two different molars with binding of the hydrogen chloride in an excess of mol of aluminum pyrimidine. Use mixed t SluraJe catch on U) to? Ö "C zs er · Pte KriktioßiRiiiife is then aJkalheh with wöfei as liUse
verwendet wird. Die ätherische Phase liefert nach dem Abdampfen ein Produkt A, das durch Umkristallisieren aus Athj !alkohol oder Alhyläther gereinigt wird.is used. The ethereal phase delivers evaporation a product A, which by recrystallization Purified from alcohol or ethyl ether will.
S- Bei der Umsetzung der Ausgangsstoffe in Anwesenheit von Pyridin wird die Mischung 1 Stunde lang auf 60 bis 70eC erhitzt. Nach teilweisem Abdampfen des Pyridins im Vakuum 6Ht das Pyridinhydrochlorid aus, das abfillriert wird. Das Filtrat wird eingedampft, S- When reacting the starting materials in the presence of pyridine, the mixture is heated to 60 to 70 ° C. for 1 hour. After partial evaporation of the pyridine in vacuo 6Ht the pyridine hydrochloride, which is filtered off. The filtrate is evaporated,
ίο und es wird so ein festes Produkt erhalten, das aus Alkohol umkristallistcrl und mil B bezeichnet wird Die so erhaltenen Produkte A und B haben denίο and it will get such a solid product that out Alcohol is recrystallized and denoted by B. The products A and B thus obtained have the
gleichen Schmelzpunkt, das gleiche IR-Spektrum undsame melting point, same IR spectrum and
geben gleiche Flecke bei der Dünnschichtchromatographic. Die Ausbeuten betragen 60% de- theoretischen, give identical spots in thin-layer chromatography. The yields are 60% de- theoretical,
Der Schmelzpunkt liegt nach dem Umkristallisieren hei loreThe melting point is hot after recrystallization
Claims (1)
1 Verfahren zur Mcr&telhing von 2*{Din*pro* pjf jcciamidoj-py rimittin. dadur c5i gekennzeichne;, daß man Z-Aminopyrirnidin mit Dipropylcsiig' *äurcch!orid ohne Anwendung von Löjungimittcln oder in Gegenwart von Pyridin pci einer Tem« pcrjjur van 60 bh 705C reagieren läöl^ iDinpropyfacctamido ^ pyrimä
1 method of mcr & telhing of 2 * {Din * pro * pjf jcciamidoj-py rimittin. dadur C5I gekennzeichne ;, that Z-Aminopyrirnidin with Dipropylcsiig '* äurcch! ORID without application of Löjungimittcln or in the presence of pyridine pci a Tem "pcrjjur van 60 70 5 C bh react läöl
Family
ID=
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