DEC0006963MA - - Google Patents
Info
- Publication number
- DEC0006963MA DEC0006963MA DEC0006963MA DE C0006963M A DEC0006963M A DE C0006963MA DE C0006963M A DEC0006963M A DE C0006963MA
- Authority
- DE
- Germany
- Prior art keywords
- vol
- ketobutyraldehyde
- basic
- basic medium
- acetals
- 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.)
- Active
Links
- 150000002357 guanidines Chemical class 0.000 claims description 3
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000008188 pellet Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLAND FEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 16. November 1951 Bekanntgemacht am 23. Februar 1956Registration date: November 16, 1951. Advertised on February 23, 1956
Cyclische Verbindungen kann man dadurch erhalten, daß man 3-Ketobutyraldehyd-i-acetale in ,saurem Medium mit organischen Stickstoffverbinrdungen umsetzt. Außerdem ist es bekannt, die Acetale von 1,3-Oxoverbindungen in alkalischem Medium umzusetzen und beispielsweise aus Ketobutyraldehyd-i-dimethylacetal und Guanidinabkömmlingen in Gegenwart von Natriumalkoholat Pyrimidinabkömmlinge zu erhalten. Bei diesen Verfahren entstellt primär das Natriumsalz des Pyrimidine, aus dem die freie Verbindung erst durch geeignete Behandlung (z.B. mit Essigsäure) gewonnen werden kann.Cyclic compounds can be obtained by that one 3-ketobutyraldehyde-i-acetals in , acidic medium with organic nitrogen compounds implements. It is also known that the acetals of 1,3-oxo compounds in alkaline Implement medium and, for example, from ketobutyraldehyde-i-dimethylacetal and guanidine derivatives in the presence of sodium alcoholate Obtain pyrimidine derivatives. In these processes, the sodium salt des is primarily disfigured Pyrimidines, from which the free compound can only be obtained by suitable treatment (e.g. with acetic acid) can be won.
Es wurde nun gefunden, daß man Pyrimidinabkömmlinge durch Umsetzung von Guanidinabkömmlingen mit 3-Ketobutyraldehyd-i-acetalen bei erhöhter Temperatur in Gegenwart von organischen Lösungsmitteln in basischem Medium vorteilhaft dadurch herstellen kann, daß man die Reaktionspartner in Abwesenheit von Fremdalkali konden- siert und das basische Medium allein durch die entsprechend bemessene Menge der verwendeten basischen Guanidinkomponente aufrechterhält. Nach diesem vereinfachten Verfahren werden die Pyrimidine in praktisch reiner Form durch Auskristallisation aus den verwendeten organischen Lösungsmitteln unmittelbar und in guter Ausbeute erhalten.It has now been found that pyrimidine derivatives can be obtained by reacting guanidine derivatives with 3-ketobutyraldehyde-i-acetals for increased Temperature in the presence of organic solvents in a basic medium is advantageous can be produced by condensing the reactants in the absence of foreign alkali siert and the basic medium solely by the correspondingly measured amount of the used basic guanidine component maintains. To This simplified process is the pyrimidines in practically pure form by crystallization from the organic ones used Solvents obtained immediately and in good yield.
45 g Guanidincarbonat werden in 300 ecm Alkohol suspendiert. Dann fügt man 66 g 3-Ketobutyraldehyd-i-dimethylacetal hinzu und erhitzt das Gemisch unter lebhaftem Rühren so lange unter Rückfluß, bis der Bodenkörper von Guanidincarbonat verschwunden ist. Die rotbraune Lösung45 g of guanidine carbonate are dissolved in 300 ecm of alcohol suspended. 66 g of 3-ketobutyraldehyde-i-dimethylacetal are then added and the mixture is refluxed with vigorous stirring until the guanidine carbonate is sedimented disappeared. The red-brown solution
509 659/76509 659/76
C 6963 IVb/12pC 6963 IVb / 12p
wird heiß filtriert; beim Erkalten kristallisiert die Hauptmenge des entstandenen 2-Amino-4-methylpyrimidins in glänzenden, weichen Kristallblättchen aus. Man saugt diese ab, wäscht mit wenig Alkohol nach und gewinnt durch Einengen der Mutterlauge einen weiteren beträchtlichen Anteil an 2-Amino-4-methyl-pyrimidin, F. 1580. Ausbeute: 41g, d.h. 75% der Theorie.is filtered hot; on cooling, most of the 2-amino-4-methylpyrimidine formed crystallizes out in shiny, soft crystal flakes. This is filtered off, washed with a little alcohol and after wins by concentrating the mother liquor a further considerable amount of 2-amino-4-methyl-pyrimidine, mp 158 0th Yield: 41 g, ie 75% of theory.
Claims (1)
Chemical Abstracts, Bd. 44 (1950), S/3455 f-h; Hoppe-Seylers, Zeitschrift für physiologische Chemie, Bd. 280 (1944), S. 126.Referred publications:
Chemical Abstracts, Vol. 44 (1950), S / 3455 fh; Hoppe-Seylers, Zeitschrift für Physiologische Chemie, Vol. 280 (1944), p. 126.
Family
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