DE1064950B - Process for the preparation of 8-oxypurines - Google Patents

Process for the preparation of 8-oxypurines

Info

Publication number
DE1064950B
DE1064950B DED24167A DED0024167A DE1064950B DE 1064950 B DE1064950 B DE 1064950B DE D24167 A DED24167 A DE D24167A DE D0024167 A DED0024167 A DE D0024167A DE 1064950 B DE1064950 B DE 1064950B
Authority
DE
Germany
Prior art keywords
weight
parts
oxypurines
preparation
yield
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.)
Pending
Application number
DED24167A
Other languages
German (de)
Inventor
Dr Alfred Dornow
Dipl-Chem Otto Hahmann
Ehrhard Hinz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ALFRED DORNOW DR
Original Assignee
ALFRED DORNOW DR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DED24066A priority Critical patent/DE1024974B/en
Application filed by ALFRED DORNOW DR filed Critical ALFRED DORNOW DR
Priority to DED24167A priority patent/DE1064950B/en
Publication of DE1064950B publication Critical patent/DE1064950B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

Verfahren zur Herstellung von 8-Oxypurinen Gegenstand des Patents 1024 974 ist ein Verfahren zur Herstellung von 2-Oxy-7-aza-benzimidazolen, welches dadurch gekennzeichnet ist, daß 2-Aminopyridincarbonsäure-(3)-amide oder -azide, deren 2ständige Aminogruppe wenigstens ein Wasserstoffatom besitzt, in üblicher Weise nach Hofmann bzw. Curtius abgebaut werden.Process for the preparation of 8-oxypurines The subject of the patent 1 024 974 is a process for the preparation of 2-oxy-7-aza-benzimidazoles, which is characterized in that 2-aminopyridinecarboxylic acid (3) -amides or azides, their 2-position Amino group has at least one hydrogen atom, can be broken down in the usual way according to Hofmann or Curtius.

Es wurde gefunden, daß entsprechende o-Aminocarbonsäureamide oder -azide von Pyrimidinen, in der gleichen Weise nach Hofmann bzw. Curtius behandelt, ebenfalls Imidazolonderivate ergeben, deren Bildung wiederum über die Stufe der Isocyanate zu erklären ist.It has been found that corresponding o-aminocarboxamides or -azides of pyrimidines, treated in the same way according to Hofmann or Curtius, also result in imidazolone derivatives, their formation in turn via the stage of Isocyanate is to be explained.

So liefern 4-Aminopyrimidin-5-carbonsäureamide bzw. -azide 8-Oxypurine in guter Ausbeute.4-aminopyrimidine-5-carboxamides or azides give 8-oxypurines in good yield.

Die Verfahrensprodukte sollen als Pharmazeutika verwendet werden.The products of the process are intended to be used as pharmaceuticals.

Beispiel 1 1,8 Gewichtsteile 2-Methyl-4-aminopyrimidin-5-carbonsäureazid werden in etwa der dreifachen Gewichtsmenge Xylol bis zum Aufhören der Stickstoffentwicklung erhitzt. Das sich dabei in fast quantitativer Ausbeute (1,45 Gewichtsteile) bildende 2-Methyl-8-oxypurin wird aus Methanol umkristallisiert. Zersetzungspunkt etwa 360° C.Example 1 1.8 parts by weight of 2-methyl-4-aminopyrimidine-5-carboxylic acid azide become about three times the amount by weight of xylene until the evolution of nitrogen ceases heated. That which forms in almost quantitative yield (1.45 parts by weight) 2-methyl-8-oxypurine is recrystallized from methanol. Decomposition point about 360 ° C.

Beispiel 2 3,5 Gewichtsteile 2-Methyl-4-aminopyrimidin-5-carbonsäureamid wurden in 50 Gewichtsteilen 10°/oiger Kalilauge suspendiert und 25 Gewichtsteile einer 15°/oigen Hypochloritlösung bei Zimmertemperatur eingetropft. Nach 2stündigem Erhitzen auf dem Wasserbad wurde filtriert und die Lösung mit Essigsäure neutralisiert. Es fielen 2,5 Gewichtsteile 2-Methyl-8-oxypurin aus. Ausbeute: 710/, der Theorie.Example 2 3.5 parts by weight of 2-methyl-4-aminopyrimidine-5-carboxamide were suspended in 50 parts by weight of 10% strength potassium hydroxide solution and 25 parts by weight of a 15% strength hypochlorite solution were added dropwise at room temperature. After heating on the water bath for 2 hours, the mixture was filtered and the solution was neutralized with acetic acid. 2.5 parts by weight of 2-methyl-8-oxypurine precipitated out. Yield: 710 /, of theory.

Beispiel 3 1,8 Gewichtsteile 2-Oxy-4-aminopyrimidin-5-carbonsäureazid wurden in 10 Gewichtsteilen Xylol bis zum Aufhören der Stickstoffentwicklung erwärmt. Das sich bildende 2,8-Dioxypurin wurde zur Reinigung in Ammoniakwasser gelöst und mit Essigsäure gefällt. F. über 400°C (Zersetzung). Ausbeute: 80°/o der Theorie.Example 3 1.8 parts by weight of 2-oxy-4-aminopyrimidine-5-carboxylic acid azide were heated in 10 parts by weight of xylene until the evolution of nitrogen ceased. The 2,8-dioxypurine that formed was dissolved in ammonia water for purification and precipitated with acetic acid. F. over 400 ° C (decomposition). Yield: 80% of theory.

Beispiel 4 1 Gewichtsteil 2,4-Diaminopyrimidin-5-carbonsäureazid wird mit 4 Gewichtsteilen trockenem Xylol 3/4 Stunden unter Rückfluß auf dem Wasserbad erhitzt. Anschließend wird noch 10 Minuten im Ölbad zum Sieden erhitzt. Nach der Abkühlung wird das feinkristalline Reaktionsprodukt abgesaugt und aus Methanol-Wasser (2: 3) umkristallisiert. Das 2-Amino-8-oxypurin bildet feine Nadeln vom F. 380'C (Zersetzung). Ausbeute: 0,85 Gewichtsteile, entsprechend 1000/, der Theorie.Example 4 1 part by weight of 2,4-diaminopyrimidine-5-carboxylic acid azide is refluxed on a water bath with 4 parts by weight of dry xylene for 3/4 hours. The mixture is then heated to boiling in an oil bath for a further 10 minutes. After cooling, the finely crystalline reaction product is filtered off with suction and recrystallized from methanol-water (2: 3). The 2-amino-8-oxypurine forms fine needles with a temperature of 380'C (decomposition). Yield: 0.85 parts by weight, corresponding to 1000 % of theory.

Claims (1)

PATENTA\SPR('CHE: Verfahren zur Herstellung von 8-Oxypurinen, dadurch gekennzeichnet, daß o-Aminocarbonsäureamide oder -azide von Pyrimidinen den Bedingungen des Hofmannschen bzw. Curtiusschen Abbaues unterworfen werden.PATENTA \ SPR ('CHE: Process for the production of 8-oxypurines, thereby characterized in that o-aminocarboxamides or azides of pyrimidines meet the conditions the Hofmann or Curtius degradation are subjected.
DED24167A 1956-10-17 1956-10-31 Process for the preparation of 8-oxypurines Pending DE1064950B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DED24066A DE1024974B (en) 1956-10-17 1956-10-17 Process for the preparation of 2-oxy-7-aza-benzimidazoles
DED24167A DE1064950B (en) 1956-10-17 1956-10-31 Process for the preparation of 8-oxypurines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DED24066A DE1024974B (en) 1956-10-17 1956-10-17 Process for the preparation of 2-oxy-7-aza-benzimidazoles
DED24167A DE1064950B (en) 1956-10-17 1956-10-31 Process for the preparation of 8-oxypurines

Publications (1)

Publication Number Publication Date
DE1064950B true DE1064950B (en) 1959-09-10

Family

ID=33098964

Family Applications (2)

Application Number Title Priority Date Filing Date
DED24066A Pending DE1024974B (en) 1956-10-17 1956-10-17 Process for the preparation of 2-oxy-7-aza-benzimidazoles
DED24167A Pending DE1064950B (en) 1956-10-17 1956-10-31 Process for the preparation of 8-oxypurines

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DED24066A Pending DE1024974B (en) 1956-10-17 1956-10-17 Process for the preparation of 2-oxy-7-aza-benzimidazoles

Country Status (1)

Country Link
DE (2) DE1024974B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10464898B2 (en) 2013-02-20 2019-11-05 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1120454B (en) * 1958-12-10 1961-12-28 Ciba Geigy Process for the preparation of 1- (ª ‰ -Di-lower alkylamino-ethyl) -2-benzyl-7-aza-benzimidazoles

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10464898B2 (en) 2013-02-20 2019-11-05 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine
US11472770B2 (en) 2013-02-20 2022-10-18 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine
US11897843B2 (en) 2013-02-20 2024-02-13 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine

Also Published As

Publication number Publication date
DE1024974B (en) 1958-02-27

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