GB744868A - Improvements relating to 4-amino-5-formamido-6-disubstituted-aminopyrimidines and acid addition salts thereof - Google Patents

Improvements relating to 4-amino-5-formamido-6-disubstituted-aminopyrimidines and acid addition salts thereof

Info

Publication number
GB744868A
GB744868A GB26314/53A GB2631453A GB744868A GB 744868 A GB744868 A GB 744868A GB 26314/53 A GB26314/53 A GB 26314/53A GB 2631453 A GB2631453 A GB 2631453A GB 744868 A GB744868 A GB 744868A
Authority
GB
United Kingdom
Prior art keywords
amino
nr1r2
pyrimidines
substituted
compounds
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
GB26314/53A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB744868A publication Critical patent/GB744868A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D239/48—Two nitrogen atoms
    • 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
    • C07D239/50—Three nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises pyrimidine derivatives of the formula <FORM:0744868/IV(a)/1> where R1 and R2 are alkyl, mononuclear aryl or mononuclear aralkyl, or with the N atom form a 6-membered ring. These are made by treating with a low temperature Raney nickel catalyst the corresponding compounds having an alkylthio or aralkylthio substituent in the 2-position. The reaction is preferably carried out in an inert solvent at 60-100 DEG C. The products form salts with strong acids such as hydrochloric, sulphuric and picric. They can be used for making purine derivatives as in Specification 744,865. Examples show the production of compounds where NR1R2 is dimethylamino, diethylamino and N-methylanilino. It is stated that R1 and R2 may be methyl, ethyl, propyl, phenyl, substituted phenyl, benzyl or substituted benzyl, and that NR1R2 may also be piperidino or morpholino. 2 - (Substituted mercapto) - 4 - amino - 5-formylamino - 6 - NR1R2 - pyrimidines are obtained from the corresponding 2:4:6-trisubstituted-pyrimidines by treatment with nitrous acid to give the 5-nitroso derivatives, reduction to 5-amino and formylation of the latter. 2 - (Substituted mercapto) - 4 - amino - 6-NR1R2-pyrimidines are made as in Specification 744,867 by treating the corresponding 6-halogen compounds with HNR1R2.
GB26314/53A 1952-10-29 1953-09-24 Improvements relating to 4-amino-5-formamido-6-disubstituted-aminopyrimidines and acid addition salts thereof Expired GB744868A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US744868XA 1952-10-29 1952-10-29

Publications (1)

Publication Number Publication Date
GB744868A true GB744868A (en) 1956-02-15

Family

ID=22119814

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26314/53A Expired GB744868A (en) 1952-10-29 1953-09-24 Improvements relating to 4-amino-5-formamido-6-disubstituted-aminopyrimidines and acid addition salts thereof

Country Status (1)

Country Link
GB (1) GB744868A (en)

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