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GB718689A - A new pyrimidine compound and the manufacture thereof - Google Patents

A new pyrimidine compound and the manufacture thereof

Info

Publication number
GB718689A
GB718689A GB5193/53A GB519353A GB718689A GB 718689 A GB718689 A GB 718689A GB 5193/53 A GB5193/53 A GB 5193/53A GB 519353 A GB519353 A GB 519353A GB 718689 A GB718689 A GB 718689A
Authority
GB
United Kingdom
Prior art keywords
chlorophenyl
ethylpyrimidine
dimethylamine
chloro
amino
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
GB5193/53A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB718689A publication Critical patent/GB718689A/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
    • C07D239/48—Two nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises 2-amino-4-dimethylamino - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine and its salts, and its preparation by reacting a 2-amino-4-halogeno - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine or a corresponding 2-acylamino derivative with dimethylamine or a salt thereof. The reaction temperature is preferably in excess of 100 DEG C. and pressure is used when employing the free dimethylamine or, alternatively, the dimethylamine may be passed in successive portions into a solution of the pyrimidine starting material in a high-boiling solvent heated to 120-150 DEG C. In examples: (1) and (2) 2-acetylamino-4-chloro - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine, dimethylamine and ethanol are heated to 160-180 DEG C. in a sealed tube or in an autoclave; (3) dimethylamine is passed into a solution of 2 - acetylamino - 4 - chloro - 5 - (41 - chlorophenyl)-6-ethylpyrimidine in phenol and the product poured into a solution of caustic soda; (4), (5) and (6) dimethylamine is passed into a suspension of 2 - acetylamino - 4 - chloro - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine in propylene glycol or 2-ethoxyethanol; and (7) 2 - amino - 4 - chloro - 5 - (41 - chlorophenyl) - 6 -ethylpyrimidine and dimethylamine hydrochloride are heated together. The 2-amino-4-chloro - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine serving as starting material is made by condensing guanidine with ethyl 2 - (41 - chlorophenyl)-3-pentanone-oate in oleum of 15 to 40 per cent concentration and subjecting the 2 - amino - 4 - hydroxy - 5 - (41 - chlorophenyl) - 6 - ethylpyrimidine so formed, or its acetyl derivative, to chlorination, e.g. with phosphorus oxychloride.
GB5193/53A 1952-03-10 1953-02-24 A new pyrimidine compound and the manufacture thereof Expired GB718689A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR718689X 1952-03-10

Publications (1)

Publication Number Publication Date
GB718689A true GB718689A (en) 1954-11-17

Family

ID=9090690

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5193/53A Expired GB718689A (en) 1952-03-10 1953-02-24 A new pyrimidine compound and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB718689A (en)

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