GB669585A - Process for the manufacture of 2-amino-4-methyl-pyrimidine and n-alkyl and n-aryl derivatives thereof - Google Patents

Process for the manufacture of 2-amino-4-methyl-pyrimidine and n-alkyl and n-aryl derivatives thereof

Info

Publication number
GB669585A
GB669585A GB13747/49A GB1374749A GB669585A GB 669585 A GB669585 A GB 669585A GB 13747/49 A GB13747/49 A GB 13747/49A GB 1374749 A GB1374749 A GB 1374749A GB 669585 A GB669585 A GB 669585A
Authority
GB
United Kingdom
Prior art keywords
methylpyrimidine
amino
guanidine
alkyl
per cent
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
GB13747/49A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB669585A publication Critical patent/GB669585A/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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2-Amino-4-methylpyrimidine and its N-alkyl and N-aryl derivatives are manufactured by condensing guanidine or a derivative thereof substituted in an amino group by an alkyl, aryl, or acyl group (the last-named, if present, being split off in the reaction) with a 4-alkoxybutene-3-ine-1, preferably in the presence of an acid condensing agent, advantageously at room temperature or slightly elevated temperatures (not above 30 DEG C.). In examples: (1) and (2) 4-ethoxy- or 4-methoxy-butenine is added with stirring to a solution of guanidine carbonate in 80 per cent sulphuric acid to produce 2-amino-4-methylpyrimidine; (3) 4-methoxybutenine is added gradually to a solution of n-butyl-guanidine sulphate in 75 per cent sulphuric acid to give 2-n-butylamino-4-methylpyrimidine; (4) 4-methoxybutenine and phenylguanidine in 80 per cent sulphuric acid yield 2-phenylamino-4-methylpyrimidine. The Specification as open to inspection under Sect. 91, comprises also references to the use of the following additional starting materials: acetyl-, benzoyl-, methyl-, ethyl- and benzyl-guanidine, and guanidines substituted by an azomethine or a cyano group; propyloxy- and butyloxy-butene-3-ine-1. This subject-matter does not appear in the Specification as accepted.
GB13747/49A 1948-05-22 1949-05-23 Process for the manufacture of 2-amino-4-methyl-pyrimidine and n-alkyl and n-aryl derivatives thereof Expired GB669585A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH669585X 1948-05-22

Publications (1)

Publication Number Publication Date
GB669585A true GB669585A (en) 1952-04-02

Family

ID=4527564

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13747/49A Expired GB669585A (en) 1948-05-22 1949-05-23 Process for the manufacture of 2-amino-4-methyl-pyrimidine and n-alkyl and n-aryl derivatives thereof

Country Status (1)

Country Link
GB (1) GB669585A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2813862A (en) * 1953-12-23 1957-11-19 Organon Process of preparation of heterocyclic compounds employing acetylene ethers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2813862A (en) * 1953-12-23 1957-11-19 Organon Process of preparation of heterocyclic compounds employing acetylene ethers

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