DE2156720A1 - Pyrimido(4,5-d) pyrimidines - prepd from polychloroalkylimino acid chloride and 4-amino uracils, are starting materials for plant - Google Patents
Pyrimido(4,5-d) pyrimidines - prepd from polychloroalkylimino acid chloride and 4-amino uracils, are starting materials for plantInfo
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- DE2156720A1 DE2156720A1 DE19712156720 DE2156720A DE2156720A1 DE 2156720 A1 DE2156720 A1 DE 2156720A1 DE 19712156720 DE19712156720 DE 19712156720 DE 2156720 A DE2156720 A DE 2156720A DE 2156720 A1 DE2156720 A1 DE 2156720A1
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- pyrimido
- optionally substituted
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- dimethyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
Description
Pyrimido [4,5-d] pyrimidine Die Erfindung betrifft neue Pyrimido [4,5-d] pyrimidine sowie ein Verfahren zu ihrer Herstellung.Pyrimido [4,5-d] pyrimidines The invention relates to new pyrimido [4,5-d] pyrimidines and a process for their preparation.
Es wurde gefunden, daß man PyrimidoE4,5-dpyrimidine erhält, wenn man Polychloralkyl-imidsäurechloride der allgemeinen Formel R¹-CCl2-N=CCl-R² (I), in der 2 @@@@@ @@@@ @@@@@e@den sein können und 1 und R für Wasserstoff, Chlor, einen Perchlormethyl-, Perchloräthyl-, Trichlorvinyl-oder einen gegebenenfalls durch Chlor oder den Trifluornethylrest ein- oder mehrfach substituierten Phenylrest stehen, mit 4-Aminouracilen der allgemeinen Formel worin R3 und R4 gleich oder verschieden sind und für gegebenenfalls substituierte aliphatische Reste mit 1 bis 12, bevorzugt 1 bis 6 C-Atomen oder gegebenenfalls substituierte aromatische Reste stehen, umsetzt.It has been found that pyrimidoE4,5-dpyrimidines are obtained when polychloroalkyl-imidic acid chlorides of the general formula R¹-CCl2-N = CCl-R² (I), in which 2 @@@@@ @@@@ @@@@ @ e @ den and 1 and R represent hydrogen, chlorine, a perchloromethyl, perchloroethyl, trichlorovinyl or a phenyl radical which is optionally substituted one or more times by chlorine or the trifluoromethyl radical, with 4-aminouracils of the general formula in which R3 and R4 are identical or different and represent optionally substituted aliphatic radicals having 1 to 12, preferably 1 to 6, carbon atoms or optionally substituted aromatic radicals.
Als aliphatische Reste R3 und R4 seien beispielsweise genannt: Gegebenenfalls substituierte geradkettige oder verzweigte Alkylreste mit 1 bis 12, insbesondere 1 bis 6 C-Atomen; z.B. der Methyl-, Äthyl-, Propyl-, Isopropyl-, Butyl-, Isobutyl- und tert.-Butylrest, die isomeren Pentyl- und iiexylreste, der Octyl- und Dodecylrest, bevorzugt jedoch der Methyl-, Äthyl-, Propyl- und Butylrest; gegebenenfalls substituierte ungesättigte Alkylreste mit bis zu 6, insbesondere bis zu 3 C-Atomen; z.B. der Vinyl- und Allylrest; gegebenenfalls substituierte cycloaliphatische Reste mit 4 bis 8 C-Atomen, bevorzugt der Cyclopentyl- und Cyclohexylrest.Examples of aliphatic radicals R3 and R4 include: Optionally substituted straight-chain or branched alkyl radicals with 1 to 12, in particular 1 to 6 carbon atoms; e.g. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl radicals, the isomeric pentyl and iiexyl radicals, the octyl and dodecyl radical, however, the methyl, ethyl, propyl and butyl radicals are preferred; optionally substituted unsaturated alkyl radicals with up to 6, in particular up to 3, carbon atoms; e.g. the vinyl and allyl radical; optionally substituted cycloaliphatic radicals with 4 to 8 C atoms, preferably the cyclopentyl and cyclohexyl radical.
Als aromatische Reste R3 und R4 seien bevorzugt der Phenyl- und Naphthylrest genannt, die gegebenenfalls ein- oder auch mehrfach substituiert sein k können.The phenyl and naphthyl radicals are preferred as aromatic radicals R3 and R4 mentioned, which can optionally be mono- or polysubstituted k.
Als Substituenten der aliphatishcen PLeste-93 und R4 seien beispielsweise genannt: Halogen (Fluor, Chlor, Brom, Jod), bevorzugt Fluor und Chlor, sowie aromatische Reste, insbesondere der Phenyl- und Naphthylrest.Examples of substituents on the aliphatic PLeste-93 and R4 are called: Halogen (fluorine, chlorine, bromine, iodine), preferably fluorine and chlorine, as well as aromatic Radicals, in particular the phenyl and naphthyl radicals.
Als Substituenten der aromatischen Reste R3 und R4 seien beispielsweise genannt: Halogen (Fluor, Chlor, Brom, Jod), bevorzugt Fluor und Chlor, Alkylgruppen mit 1 bis 6, bevorzugt 1 bis 3 C-Atomen, Halogenalkylreste mit 1 bis 3 C-Atomen, bevorzugt der Trifluormethylrest.Examples of substituents on the aromatic radicals R3 and R4 are called: halogen (fluorine, chlorine, bromine, iodine), preferably fluorine and chlorine, alkyl groups with 1 to 6, preferably 1 to 3 carbon atoms, haloalkyl radicals with 1 to 3 carbon atoms, preferably the trifluoromethyl radical.
Die nach dem erfindungsgemäßen Verfahren erhältlichen neuen Pyrimido4,5-djpyrimidine entsprechen der allgemeinen Formel in der R1 bis R4 die oben angegebene Bedeutung besitzen.The new pyrimido4,5-djpyrimidines obtainable by the process according to the invention correspond to the general formula in which R1 to R4 have the meaning given above.
Das erfindungsgemäße Verfahren wird im Temperaturbereich von etwa 0° bis etwa 2500C, vorzugsweise von etwa 800 bis etwa 2000C durchgeführt.The inventive method is in the temperature range of about 0 ° to about 2500C, preferably from about 800 to about 2000C.
Das Verfahren kann sowohl drucklos als auch bei erhöhtem Druck im Autoklaven durchgeführt werden, wobei im letzteren Fall der entstehende Chlorwasserstoff über ein Entspannungsventil unter Einhaltung des gewählten Reaktionsdrucks kontinuierlich abgeführt wird.The process can be either pressureless or with increased pressure in the Autoclaves are carried out, in the latter case the resulting hydrogen chloride continuously via an expansion valve while maintaining the selected reaction pressure is discharged.
Im allgemeinen werden das Polychloralkyl-.imidsäurechlorid und das 4-Aminouracil im Molverhältnis von 1 : 1 bis 4 : 1, bevorzugt jedoch im Molverhältnis von etwa 1: 1, umgesetzt; man erhitzt für etwa 1 bis 4 Stunden, jedoch wenigstens bis zur Beendigung der HCl-Entwickhung, die nach bekannten Methcden festgestellt werden kann, au etwa 0o bis etwa 2500C, vorzugsweise auf etwa 800 bis etwa 2000C Das erfindungsgemät?e Verfahren wird bevorzugt in einem chemisch indifferenten Verdiinnungsmittel durchgeführt; als solche kommen bevorzugt in Betrach-t: Toluol, Chlorbenzol, o-Dichlorbenzol, Nitrobenzol und Tetramethylensulfon. Ferner kann bei der Umsetzung mit Trichlormethylisocyariiddichlorid dieses im Überschuß als Verd2nnungsmittel dienen.In general, the polychloroalkyl imidyl chloride and the 4-aminouracil in a molar ratio of 1: 1 to 4: 1, preferred however in a molar ratio of about 1: 1, reacted; it is heated for about 1 to 4 hours, but at least until the evolution of HCl has ended, according to known methods can be determined au about 0o to about 2500C, preferably to about 800 to about 2000C The inventive method is preferred in a chemically indifferent Thinners carried out; as such are preferred: toluene, Chlorobenzene, o-dichlorobenzene, nitrobenzene and tetramethylene sulfone. Furthermore, at the reaction with Trichloromethylisocyariiddichlorid this in excess as a diluent to serve.
Da bei der Umsetzung Chlorwasserstoff entsteht, können die Verwendung findenden 4-Aminouracile selbstverständlich auch in Form ihrer chlorwasserstoffsauren Salze eingesetzt werden.Since hydrogen chloride is produced during the reaction, the use Finding 4-aminouracils of course also in the form of their hydrochloric acids Salts are used.
Die nach dem erfindungsgemäßen Verfahren erhaltenen Pyrimido-64,5-ddpyrimidine können leicht nach bekannten Methoden aus der Reaktionslösung, z.B. durch Verdampfen des Lösungsmittels, isoliert bzw. z.B. durch Umkristallisieren gereinigt werden.The pyrimido-64,5-ddpyrimidines obtained by the process according to the invention can easily be removed from the reaction solution by known methods, e.g. by evaporation of the solvent, isolated or purified e.g. by recrystallization.
Das erfindungsgemäße Verfahren sei am Beispiel der Umsetzung von 1,5-Dimethyl-4-aminouracil mit Trichlormethylisocyaniddichlorid erläutert: Die als Ausgangsmaterialien Verwendung findenden Polychoralkylimidsäurechloride sind leicht erhältlich (Neuere Methoden der präparativen organischen Chemie, Bd. VI, S. 1 (1970)); beispielsweise seien genannt: Dichlormethylisocyaniddichlorid, N-Pentachloräthylisocyaniddi chlorid, α, α-Dichlorbenzylisochyaniddichlorid, α, α-Dihclorpenta-chlorbenzyl-isocyaniddichlorid, Pentachlorallylisocyaniddichlorid, α, α-dichlor-o-chlorbenzylisocyaniddichlorid, α, α Dichlor-m-chlorbenzylisocyaniddichlorid, Dichlor-p-chlorbenzylisocyaniddichlorid, α, α-Dichlor-3,4-dichlorbenzylisocyaniddichlorid, α, α-Dichlor-m-trifluormethylbenzyl-isocyanid dichlorid, N-Penta-chloräthyltrichloracetimidsäurechlorid, N-(α, α-Dichlorbenzyl)-ttichloracetimidsäurechlorid, N-alpha; (-Dichlor-2-chlorbenzyl)-ttichloracetimidsäurechlorid, besonders bevorzugt ist Trichlormethyl-isocyaniddichlorid.The process according to the invention is illustrated using the example of the reaction of 1,5-dimethyl-4-aminouracil with trichloromethyl isocyanide dichloride: The polychloroalkylimidyl chlorides used as starting materials are readily available (Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 1 (1970)); Examples include: dichloromethyl isocyanide dichloride, N-pentachloroethyl isocyanide di chloride, α, α-dichlorobenzyl isochyanide dichloride, α, α-dichloropenta-chlorobenzyl isocyanide dichloride, pentachloroallyl isocyanide dichloride, α, α-dichloro-o-chlorobenzyl isocyanide dichloride, α, α-dichloro-dichloride dichloride dichloride, α-chlorobenzyl isocyanide dichloride, α-chlorobenzyl isocyanide dichloride, α, α-dichloro-dichloride dichloride dichloride, α-chlorobenzyl isocyanide dichloride, α, α-dichlorobenzylisochyanide dichloride p-chlorobenzyl isocyanide dichloride, α, α-dichloro-3,4-dichlorobenzyl isocyanide dichloride, α, α-dichloro-m-trifluoromethylbenzyl isocyanide dichloride, N-penta-chloroethyltrichloroacetimidic acid chloride, N- (α, α-dichlorobenzyl) -alpha-dichloroacetimidic acid chloride ; (-Dichlor-2-chlorobenzyl) -ttichloroacetimidic acid chloride, trichloromethyl isocyanide dichloride is particularly preferred.
Ebenso sind die als Ausgangsmaterialien Verwendung findenden 4-Aminouracile bekannt oder können'auf einfache Weise durch Umsetzung von Harnstoff-Derivaten mit Cyanessigsäure oder Cyanessigsäureestern erhalten werden (Journal für org Chemie, 16, 1879-1890 (1951)).The 4-aminouracils used as starting materials are also used known or can 'in a simple manner by reacting urea derivatives with Cyanoacetic acid or cyanoacetic acid esters are obtained (Journal für org Chemie, 16, 1879-1890 (1951)).
In der erfindungsgemäßen Umsetzung finden bevorzugt Verwendung: 1, 3-Dimethyl-4-aminouacil, 1, 3-Di-n- propyl-4-amonouracil, 1-Methyl-3-cyclohexyl-4-aminouracil, 1-Methyl-3-benzyl-4-aminouracil, 1-Methyl-3-phenyl-4-aminouracil, 1-methyl-3-p-chlorphenyl-4-aminouracil, 1-Methyl-3-methallyl-4-aminouracil, 1-Methyl-3-n-butyl-4-aminouracil, 1,3-Di-n-butyl-4-aminouracil, 1 , 3-Diallyl-4-aminouracil, 1-Methyl-3-i-butyl-4-aminouracil, 1-methyl-3-n-propyl-4-aminouracil, 1-Methyl-3-p-tolyl-4-aminouracil, 1,3-Dibenzyl-4-aminouracil, 1,3-Bis-(B-phenäthylp4-aminouraoil.The following are preferably used in the implementation according to the invention: 1, 3-dimethyl-4-aminouacil, 1,3-di-n-propyl-4-amonouracil, 1-methyl-3-cyclohexyl-4-aminouracil, 1-methyl-3-benzyl-4-aminouracil, 1-methyl-3-phenyl-4-aminouracil, 1-methyl-3-p-chlorophenyl-4-aminouracil, 1-methyl-3-methallyl-4-aminouracil, 1-methyl-3-n-butyl-4-aminouracil, 1,3-di-n-butyl-4-aminouracil, 1,3-diallyl-4-aminouracil, 1-methyl-3-i-butyl-4-aminouracil, 1-methyl-3-n-propyl-4-aminouracil, 1-methyl-3-p-tolyl-4-aminouracil, 1,3-dibenzyl-4-aminouracil, 1,3-bis- (B-phenethylp4-aminouraoil.
Die nach dem erfindungsgemEßen Verfahren erhältlichen neuen Pyrimido [4,5 -d] pyrimidine sind wertvolle Ausgangsprodukte für die Synthese von pfianzenschutmitteln.The new pyrimido obtainable by the process of the invention [4,5 -d] pyrimidines are valuable starting materials for the synthesis of plant protection agents.
Beispiel.Example.
In den folgenden Beispielen 1-5 wird entsprechend nachstehender allgemeiner Vorschrift gearbeitet: 1 Mol 4-Aminouracil wird in 150 ml bis 250 ml trockenem o-Dichlorbenzol suspendiert und unter Eiskühlung und Rühren bei 100 bis 200 C tropfen- oder portionsweise mit 1 Mol Polychloralkyl-imidsäurechlorid versetzt und innerhalb von etwa einer Stunde auf 1500 bis 1600 C erhitzt, wobei heftige Chlorwasserstoff-Entwicklung eintritt. Bis zur Beendigung der Chlorwasserstoff-Entwicklung wird anschließend noch etwa 1 bis 2 Stunden auf 1600 C bis 1800 C erhitzt. Das erhaltene Reaktionsgemisch wird mit 200 ml trockenem Leichtbenzin (Siedepunkt 500 bis 700 C) versetzt, der Niederschlag abgesaugt und mehrmals mit trockenem Petroläther (Siedepunkt 300 bis 500 C) gewaschen.In the following examples 1-5, the following becomes correspondingly more general Procedure worked: 1 mol of 4-aminouracil is in 150 ml to 250 ml of dry o-dichlorobenzene suspended and while cooling with ice and stirring at 100 to 200 C dropwise or in portions with 1 mole of polychloroalkyl-imidic acid chloride and within about one Heated to 1500 to 1600 C for an hour, with vigorous evolution of hydrogen chloride. Until the end of the evolution of hydrogen chloride, about Heated to 1600 C to 1800 C for 1 to 2 hours. The reaction mixture obtained is 200 ml of dry mineral spirits (boiling point 500 to 700 C) are added, the precipitate Sucked off and washed several times with dry petroleum ether (boiling point 300 to 500 C).
Das Rohprodukt wird durch Umkristallisation gereinigt.The crude product is purified by recrystallization.
Beispiel 1: Aus 1 Mol 1,3-Dimethyl-4-aminouracil und 1 Mol Trichlormethylisocyaniddichlorid werden 248 g (95 % d.Th.) 1,3-Dimethyl-5,7-dichlor-pyrimido,5-dpyrimidin vom Schmelzpunkt 1860 C erhalten.Example 1: From 1 mol of 1,3-dimethyl-4-aminouracil and 1 mol of trichloromethyl isocyanide dichloride 248 g (95% of theory) 1,3-dimethyl-5,7-dichloro-pyrimido, 5-dpyrimidine have a melting point Preserved 1860 C.
Beispiel 2: a.) Aus 1 Mol 1,3-Bis-(B-phenäthyl)-4-aminouracil und 1 Mol Trichlormethylisocyaniddichlorid werden 376 g (85 % d.Th.) 1,3-Bis-(B-phenäthyl)-5,7 -dichlorpyrimide 4,- 5-d pyrimidin vom Schmelzpunkt 1470 C erhalten.Example 2: a.) From 1 mol of 1,3-bis- (B-phenethyl) -4-aminouracil and 1 mol of trichloromethyl isocyanide dichloride is 376 g (85% of theory) of 1,3-bis (B-phenethyl) -5.7 -dichloropyrimide 4, -5-d pyrimidine with a melting point of 1470 C.
Das Verwendung findende Uracil wird wie folgt hergestellt:-b. ) 155 g N, N'-Bis-(B-phenäthyl)-harnstoff, 57,8 g Cyanessigsäure und 170 ml Acetanhydrid werden 2 Stunden auf 800 C erhitzt. Überschüssiges Acetanhydrid und gebildete Essigsäure werden bei einer Badtemperatur von 800 C abdestilliert, der Rückstand mit 50 ml Wasser versetzt und erneut zur Trockene gebracht. Man gibt 280 ml Wasser zu und macht mit konzentrierter NaOH alkalisch. Der Niederschlag wird abgesaugt, mit H20 gewaschen und 24 Stunden bei 800 C i. Vak. getrocknet.The uracil used is produced as follows: -b. ) 155 g of N, N'-bis (B-phenethyl) urea, 57.8 g of cyanoacetic acid and 170 ml of acetic anhydride are heated to 800 C for 2 hours. Excess acetic anhydride and acetic acid formed are distilled off at a bath temperature of 800 C, the residue with 50 ml Water was added and brought to dryness again. 280 ml of water are added and makes alkaline with concentrated NaOH. The precipitate is filtered off with suction, with H20 washed and 24 hours at 800 C i. Vac. dried.
Nach Umkristallisieren aus Äthanol werden 128 g (66 % d.Th.) 1,3-Bis-(ß-phenäthyl)-4-aminouracil in Form farbloser Kristalle vom Schmelzpunkt 2010 bis 203° C erhalten. Analyse: C20H21N302 (335) Ber.: C 71,6 H 6,27 N 12,5 Gef.: C 71,7 H 6,5 N 12,4 Beispiel 3: Aus 1 Mol 1-Methyl-3-phenyl-4-aminouracil und 1 Mol Trichlormethyl-isocyaniddichlorid werden 290 g (90 $ d.Th.) 1-Methyl-3-phenyl-5,7-dichlorpyrimido [4,5-d] pyrimidin vom Schmelzpunkt 1920 C erhalten. After recrystallization from ethanol, 128 g (66% of theory) of 1,3-bis- (β-phenethyl) -4-aminouracil are obtained obtained in the form of colorless crystals with a melting point of 2010 to 203 ° C. Analysis: C20H21N302 (335) Calc .: C 71.6 H 6.27 N 12.5 Found: C 71.7 H 6.5 N 12.4 Example 3: From 1 mole of 1-methyl-3-phenyl-4-aminouracil and 1 mole of trichloromethyl isocyanide dichloride 290 g ($ 90 of theory) 1-methyl-3-phenyl-5,7-dichloropyrimido [4,5-d] pyrimidine are obtained obtained with a melting point of 1920 ° C.
Beispiel 4: Aus 1 Mol 1,3-Dimethyl-4-aminouracil und 1 Mol N-Pentachloräthyl-trichloracetimideäurschlorid und 1 Mol 1,3-Dimethyl-4 aminouracil werden 363 g (95 % d.Th.) 1,3-Dimethyl-5,7-bis-(trichlormethyl)-pyrimido[4,5-d] pyrimidin vom Schmelzpunkt 1490 C erhalten.Example 4: From 1 mol of 1,3-dimethyl-4-aminouracil and 1 mol of N-pentachloroethyl-trichloroacetimide acid chloride and 1 mole of 1,3-dimethyl-4 aminouracil are 363 g (95% of theory) 1,3-dimethyl-5,7-bis (trichloromethyl) pyrimido [4,5-d] pyrimidine with a melting point of 1490.degree.
Beispiel 5: Aus 1 Mol 1 ,3-Dimethyl-4-aminouracil und 1 Mol α, α-Dichlorbenzyl-isocyaniddichlorid werden 242 g (80 % d.Th.) 1,3-Dimethyl-5-phenyl-7-chlorpyrimido [4,5 -d] pyrimidin und 1 , 3-Dimethyl-5-chlor-7-phenylpyrimido [4,5-d] pyrimidin vom Schmelzpunkt 1740 bis 1770 C erhalten.Example 5: From 1 mol of 1,3-dimethyl-4-aminouracil and 1 mol of α, α-Dichlorobenzyl isocyanide dichloride is 242 g (80% of theory) of 1,3-dimethyl-5-phenyl-7-chloropyrimido [4,5 -d] pyrimidine and 1,3-dimethyl-5-chloro-7-phenylpyrimido [4,5-d] pyrimidine obtained from melting point 1740 to 1770 C.
Beispiel 6: Umsetzung von 1,3-Dimethyl-4-aminouracil mit überschüssigem Trichlormethylisocyaniddichlorid.Example 6: Reaction of 1,3-dimethyl-4-aminouracil with excess Trichloromethyl isocyanide dichloride.
31 g (0,2 Mol) 1,3-Dimethyl-4-aminouracil und 129 g (0,6 Mol) Trichlormethylisocyaniddichlorid werden bis zur Beendigung der HCl-Entwicklung unter Rückfluß zum Sieden erhitzt. Dann wird bei 0° bis 100 C mit 60 ml Petroläther (Siedepunkt 300 bis 500 C) versetzt, der gebildete Niederschlag abgesaugt und mehrmals mit Petroläther gewaschen. Man erhält 49,6 g .(95 % d.Th.) 1,3-Dimethyl-5,7-dichlor-pyrimido 4,5-d pyrimidin vom Schmelzpunkt 1860 C.31 g (0.2 mole) 1,3-dimethyl-4-aminouracil and 129 g (0.6 mole) trichloromethyl isocyanide dichloride are refluxed until the evolution of HCl has ended. Then 60 ml of petroleum ether (boiling point 300 to 500 C) are added at 0 ° to 100 ° C. the precipitate formed is filtered off with suction and washed several times with petroleum ether. Man receives 49.6 g. (95% of theory) 1,3-dimethyl-5,7-dichloro-pyrimido 4,5-d pyrimidine vom Melting point 1860 C.
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1971
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