GB775370A - New pyrimidine derivatives and processes for their preparation - Google Patents

New pyrimidine derivatives and processes for their preparation

Info

Publication number
GB775370A
GB775370A GB1921954A GB1921954A GB775370A GB 775370 A GB775370 A GB 775370A GB 1921954 A GB1921954 A GB 1921954A GB 1921954 A GB1921954 A GB 1921954A GB 775370 A GB775370 A GB 775370A
Authority
GB
United Kingdom
Prior art keywords
hexane
oxy
decane
amino
product
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
GB1921954A
Inventor
Robert Michel Jacob
Gilbert Louis Regnier
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
Priority to GB1921954A priority Critical patent/GB775370A/en
Publication of GB775370A publication Critical patent/GB775370A/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
    • C07D239/47—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
    • 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
    • C07D239/52—Two oxygen 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
    • C07D239/56—One oxygen atom and one sulfur 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
    • C07D239/60—Three or more oxygen or sulfur atoms

Landscapes

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

Abstract

The invention comprises: (a) pyrimidien derivatives of the general formula: <FORM:0775370/IV(b)/1> wherein A represents a straight or branched chain aliphatic hydrocarbon group of 2 to 12 (preferably 6 to 10) carbon atoms, R represents an amino or mercapto group, and R1 represents a halogen atom, a hydroxy, lower (1-4 C) alkoxy, mercapto or primary, secondary or tertiary amino group, or (when R is amino) a hydrogen atom, and their acid addition salts; (b) the manufacture of the compounds in which R1 is a hydroxy group by condensing a di-(ethoxycarbonylformylmethoxy)-alkane of the formula: <FORM:0775370/IV(b)/2> with thiourea or guanidine; (c) manufacture of compounds in which R1 has the other specified meanings in accordance with the examples below. The process may be effected by heating the reactants (the first of which may be prepared in situ and used in the form of its sodium derivative) in ethanol under reflux in the presence of sodium or potassium ethoxide, and may be followed by replacement of the hydroxy group (R1) by halogen (optionally after acetylation when R is NH2) and, if desired, reaction of the halogen derivative with ammonia, a primary or secondary amine or an alkali metal alcoholate or hydrosulphide. The products have bactericidal and anthelmintic (schistosomicidal) properties. In examples: (1) a mixture of 1 : 6-di-(ethoxycarbonylmethoxy)-hexane and ethyl formate is run into a suspension of sodium in ether, the precipitated 1 : 6 - di - (ethoxycarbonylformylmethoxy) - hexane (sodium derivative) is dissolved in alcohol and the solution refluxed with guanidine and potassium ethoxide to produce 1 : 6 - di - (21 - amino - 41 - hydroxypyrimidyl - 51-oxy)-hexane, the hydrochloride of which is described; (2) 1 : 10 - di - (ethoxycarbonylmethoxy)-decane similarly yields 1 : 10-di-(21-amino41 - hydroxypyrimidyl - 51 - oxy) - decane and its hydrochloride; (3) the product of (1) is acetylated with acetic anhydride and pyridine, the diacetyl derivative is treated with POCl3 and the product is hydrolysed with aqueous caustic soda to 1 : 6-di-(21-amino-41-chloropyrimidyl - 51 - oxy) - hexane, which is purified by conversion to its hydrochloride; (4) the product of (2) is similarly converted to 1 : 10-di-(21-acetylamino - 41 - chloropyrimidyl - 51 - oxy)-decane, which is heated with alcoholic ammonia to form 1 : 10 - di - (21 : 41 - diaminopyrimidyl-51 - oxy) - decane; (5) 1 : 6 - di - (21 - acetylamino - 41 - chloropyrimidyl - 51 - oxy) - hexane is heated with alcoholic ammonia to give 1 : 6-di-(21 : 41 - diaminopyrimidyl - 51 - oxy) - hexane the ammonia may be replaced by (6) dimethylamine; and (7) di-n-butylamine; (8) the ammonia in (4) is replaced by di-n-butylamine; (9) the guanidine in (1) is replaced by thiourea, producing 1 : 6 - di - (21 - mercapto - 41 - hydroxypyrimidyl - 51 - oxy) - hexane; (10) the product of (3) is heated with a solution of sodium in butanol to form 1 : 6-di-(21-amino-41-butoxypyrimidyl - 51 - oxy) - hexane; (11) the product of (3) is hydrogenated in aqueous ethanol in the presence of a palladium on calcium carbonate catalyst to give 1 : 6-di-(21-aminopyrimidyl - 51 - oxy) - hexane; (12) the product of (3) is heated with potassium hydrosulphide in ethanol to produce 1 : 6-di-(21 amino-41-mercaptopyrimidyl-51-oxy)-hexane. Starting materials. 1 : 6-Di-(ethoxycarbonylmethoxy) hexane is obtained by the action of ethanol in acidic medium on 1 : 6-di(cyanomethoxy) hexane, itself obtained by the action of cuprous cyanide on hexane-1 : 6-diol di-chloromethyl ether. The analogous decane derivatives are obtained similarly. The chloromethyl diether of decane-1 : 10-diol is obtained by reacting paraformaldehyde and anhydrous hydrogen chloride with decane-1 : 10-diol.
GB1921954A 1954-06-30 1954-06-30 New pyrimidine derivatives and processes for their preparation Expired GB775370A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1921954A GB775370A (en) 1954-06-30 1954-06-30 New pyrimidine derivatives and processes for their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1921954A GB775370A (en) 1954-06-30 1954-06-30 New pyrimidine derivatives and processes for their preparation

Publications (1)

Publication Number Publication Date
GB775370A true GB775370A (en) 1957-05-22

Family

ID=10125708

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1921954A Expired GB775370A (en) 1954-06-30 1954-06-30 New pyrimidine derivatives and processes for their preparation

Country Status (1)

Country Link
GB (1) GB775370A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248619A (en) * 1978-08-08 1981-02-03 Ici Australia Limited Bis[pyrimidyloxy(thio)]benzene derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248619A (en) * 1978-08-08 1981-02-03 Ici Australia Limited Bis[pyrimidyloxy(thio)]benzene derivatives

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