GB798646A - Improvements in and relating to derivatives of pyrimidine and the manufacture thereof - Google Patents

Improvements in and relating to derivatives of pyrimidine and the manufacture thereof

Info

Publication number
GB798646A
GB798646A GB2305555A GB2305555A GB798646A GB 798646 A GB798646 A GB 798646A GB 2305555 A GB2305555 A GB 2305555A GB 2305555 A GB2305555 A GB 2305555A GB 798646 A GB798646 A GB 798646A
Authority
GB
United Kingdom
Prior art keywords
gives
hydroxy
amino
compound
mercapto
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
Application number
GB2305555A
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB2305555A priority Critical patent/GB798646A/en
Publication of GB798646A publication Critical patent/GB798646A/en
Priority to GB19863/62A priority patent/GB975850A/en
Priority to US633399A priority patent/US3626064A/en
Priority to US658641A priority patent/US3497307A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0798646/IV (b)/1> wherein R1 and R2 are the same or different and are hydroxy, mercapto, lower alkylmercapto, amino, lower alkylamino or di-(lower alkyl)-amino groups (the lower alkyl groups containing 1 to 4 carbon atoms) or either but not both may be hydrogen, and their acid-addition salts. In examples, pyrazole-3 : 4-dicarboxylic acid is refluxed with thionyl chloride, the excess thionyl chloride is removed, the residue is reacted with ammonia in t-butanol at 0 DEG C. and the resulting precipitate is boiled with ammonium hydroxide to give pyrazole-3 : 4-dicarboxamide; with sodium hypochlorite solution at 0 DEG C. and subsequent acidification this gives 4 : 6-dihydroxy-1-pyrazolo-(3,4-d)pyrimidine from which the 4-mercapto-6-hydroxy compound is obtained by refluxing with phosphorus pentasulphide in pyridine; the latter compound on heating with dimethylamine in ethanol at 130 DEG C. gives the 4-dimethylamino-6-hydroxy compound; the 4 - amino - 6 - hydroxy compound is similarly obtained by reaction with ammonia in alcohol at 143 DEG C. and, from the 4-mercapto-6-hydroxy compound and phosphorus pentasulphide in pyridine the 4 : 6-dimercapto compound is prepared; the latter with ammonia in alcohol at 149 DEG C. gives the 4-amino-6-mercapto compound and this on refluxing with ammonium hydroxide and Raney nickel gives 4-amino-1-pyrazolo - (3,4 - d)-pyrimidine (isolated as the hydrochloride); the latter on heating with dilute sulphuric acid and potassium nitrite gives the corresponding 4-hydroxy compound: 4 - hydroxy - 6 - mercapto - 1 - pyrazolo - (3,4-d)-pyrimidine is prepared by heating 3- amino-4-pyrazole carboxamide with thiourea and gives, with methyl iodide in sodium hydroxide solution at room temperature, the 4-hydroxy-6-methylmercapto compound which, with ammonium hydroxide at 140 DEG C. gives 4-hydroxy-6-amino-1-pyrazolo-(3,4-d)pyrimidine.
GB2305555A 1955-08-10 1955-08-10 Improvements in and relating to derivatives of pyrimidine and the manufacture thereof Expired GB798646A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB2305555A GB798646A (en) 1955-08-10 1955-08-10 Improvements in and relating to derivatives of pyrimidine and the manufacture thereof
GB19863/62A GB975850A (en) 1955-08-10 1962-05-23 Xanthine oxidase inhibitors
US633399A US3626064A (en) 1955-08-10 1967-04-25 Treatment of hyperuricema with 4-amino-6-hydroxy-1-h-pyrazolo(3,4-d)pyrimidine
US658641A US3497307A (en) 1955-08-10 1967-08-07 Method of preventing oxidation of 6-substituted purines with 4-hydroxy-1h-pyrazolo(3,4-d)pyrimidine and 4,6 - dihydroxy-1h-pyrazolo(3,4-d)pyrimidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2305555A GB798646A (en) 1955-08-10 1955-08-10 Improvements in and relating to derivatives of pyrimidine and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB798646A true GB798646A (en) 1958-07-23

Family

ID=10189376

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2305555A Expired GB798646A (en) 1955-08-10 1955-08-10 Improvements in and relating to derivatives of pyrimidine and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB798646A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0000541A2 (en) * 1977-07-20 1979-02-07 The Wellcome Foundation Limited 1H-Pyrimido-(4,5-c)-1,2-diazepines, methods for their preparation and compositions containing them; their use as intermediates for heterocyclic transformations.
US4260758A (en) 1979-09-17 1981-04-07 Burroughs Wellcome Co. Pyrazolo (3,4-d) pyrimidines and methods of making

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0000541A2 (en) * 1977-07-20 1979-02-07 The Wellcome Foundation Limited 1H-Pyrimido-(4,5-c)-1,2-diazepines, methods for their preparation and compositions containing them; their use as intermediates for heterocyclic transformations.
EP0000541A3 (en) * 1977-07-20 1979-07-11 The Wellcome Foundation Limited 1h-pyrimido-(4,5-c)-1,2-diazepines, methods for their preparation and compositions containing them; their use as intermediates for heterocyclic transformations.
US4237289A (en) 1977-07-20 1980-12-02 Burroughs Wellcome Co. 2,7-Diamino-8-methyl-5-substituted pyrido{2,3-d}pyrimidin-6-ones
US4288365A (en) 1977-07-20 1981-09-08 Burroughs Wellcome Co. Pyrido derivatives
US4315932A (en) 1977-07-20 1982-02-16 Burroughs Wellcome Co. Method of using 1H-pyrimido-4,5-c -1,2-diazepines as antibacterial and anticoccidocidal agents
US4260758A (en) 1979-09-17 1981-04-07 Burroughs Wellcome Co. Pyrazolo (3,4-d) pyrimidines and methods of making

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