GB684759A - Improvements in and relating to the synthesis of derivatives of pyrimidine - Google Patents

Improvements in and relating to the synthesis of derivatives of pyrimidine

Info

Publication number
GB684759A
GB684759A GB10570/49A GB1057049A GB684759A GB 684759 A GB684759 A GB 684759A GB 10570/49 A GB10570/49 A GB 10570/49A GB 1057049 A GB1057049 A GB 1057049A GB 684759 A GB684759 A GB 684759A
Authority
GB
United Kingdom
Prior art keywords
ethyl
chlorophenoxy
carbon atoms
naphthoxy
reacting
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
GB10570/49A
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.)
SmithKline Beecham Corp
Original Assignee
Burroughs Wellcome Co USA
Burroughs Wellcome and Co USA Inc
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 Burroughs Wellcome Co USA, Burroughs Wellcome and Co USA Inc filed Critical Burroughs Wellcome Co USA
Priority to GB10570/49A priority Critical patent/GB684759A/en
Publication of GB684759A publication Critical patent/GB684759A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • C07D239/50—Three nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pest Control & Pesticides (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises pyrimidines of the formula <FORM:0684759/IV (b)/1> where R is hydrogen, alkyl (1-3 carbon atoms), aryl (not over 7 carbon atoms) or haloaryl (not over 6 carbon atoms) and Ar is aryl, haloaryl, hydroxyaryl, alkoxyaryl, alkylaryl or carbethoxyaryl with 6-13 carbon atoms and not over 2 rings. These are made by condensing an a -aryloxy-b -formyl- or keto-carboxylic ester with guanidine to give the corresponding 4-hydroxy compound; this is then converted into the 4-chloro or 4-thio-derivative with phosphorus oxychloride or pentasulphide (as in Specification 598,514) and finally treated with ammonia to introduce the 4-amino group. Examples show the production of the following 2 : 4-diaminopyrimidines: 5-p-chlorophenoxy, 5 - m - chlorophenoxy, 5 - o - chlorophenoxy, 5-(21 : 41-dichlorophenoxy), 5 - b - naphthoxy, 5-p-benzylphenoxy, 5 - p - phenylphenoxy, 5 - p - chlorophenoxy-6-methyl, 5-(61-bromo-21-naphthoxy)-6-phenyl and 5-p-carbethoxyphenoxy; the corresponding 4-hydroxy and 4-chloro compounds are intermediates. 2-Amino-4-thio-5-p-chlorophenoxypyrimidine is also described. The a -formyl derivatives of ethyl p-chlorophenoxyacetate, ethyl b -naphthoxyacetate and ethyl p-carbethoxyphenoxyacetate are prepared by reacting the esters with ethyl formate. Ethyl a -(p-chlorophenoxy)-acetoacetate is made by reacting ethyl a -chloroacetoacetate with sodium p-chlorophenolate. Ethyl a -(6-bromo-2-naphthoxy)-benzoylacetate is made similarly. According to the Provisional Specification, the pyrimidines of the above formula (R=H) can be made by reacting an aryloxymalonic ester with guanidine, replacing the two hydroxyl groups by chlorine, treating the product with ammonia to give a 2 : 4-diamino-5-aryloxy-6-chloro-pyrimidine and finally eliminating the chlorine atom by reduction.
GB10570/49A 1949-04-21 1949-04-21 Improvements in and relating to the synthesis of derivatives of pyrimidine Expired GB684759A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB10570/49A GB684759A (en) 1949-04-21 1949-04-21 Improvements in and relating to the synthesis of derivatives of pyrimidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB10570/49A GB684759A (en) 1949-04-21 1949-04-21 Improvements in and relating to the synthesis of derivatives of pyrimidine

Publications (1)

Publication Number Publication Date
GB684759A true GB684759A (en) 1952-12-24

Family

ID=9970278

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10570/49A Expired GB684759A (en) 1949-04-21 1949-04-21 Improvements in and relating to the synthesis of derivatives of pyrimidine

Country Status (1)

Country Link
GB (1) GB684759A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4850912B2 (en) * 2005-09-01 2012-01-11 エフ．ホフマン−ラ ロシュ アーゲー Diaminopyrimidines as P2X3 and P3X2 / 3 modulators

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4850912B2 (en) * 2005-09-01 2012-01-11 エフ．ホフマン−ラ ロシュ アーゲー Diaminopyrimidines as P2X3 and P3X2 / 3 modulators

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