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GB953876A - Preparation of 4-amino-5-(lower alkoxy)-methyl-2-propyl-pyrimidines - Google Patents

Preparation of 4-amino-5-(lower alkoxy)-methyl-2-propyl-pyrimidines

Info

Publication number
GB953876A
GB953876A GB34753/62A GB3475362A GB953876A GB 953876 A GB953876 A GB 953876A GB 34753/62 A GB34753/62 A GB 34753/62A GB 3475362 A GB3475362 A GB 3475362A GB 953876 A GB953876 A GB 953876A
Authority
GB
United Kingdom
Prior art keywords
methyl
alkoxy
propyl
alkali metal
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
GB34753/62A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB953876A publication Critical patent/GB953876A/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
    • C07D239/30—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/20—Inorganic substances, e.g. oligoelements
    • A23K20/24—Compounds of alkaline earth metals, e.g. magnesium
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
    • A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Food Science & Technology (AREA)
  • Birds (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

4-Amino-5-[(C1-7 alkoxy)-methyl]-2-propyl-pyrimidines are prepared by either of the following two methods, viz:-(1) by reacting butyramidine hydrochloride (obtained by the action of hydrogen chloride, a C1-7 alkanol and ammonia on butyronitrile) with an alkali metal salt of a C1-7 alkyl a -(C1-7 alkoxy)-methyl-b -hydroxyacrylate (obtained by introduction of a C1-7 alkylacrylate, a C1-7 alkyl formate and an alkali metal C1-7 alkoxide), treating the resulting 4-hydroxy-5-[(C1-7 alkoxy)-methyl]-2-propyl-pyrimidine with phosphorus oxychloride and aminating the 4-halogen-5-[(C1 7 alkoxy)-methyl]-2-propyl-pyrimidine thus obtained with concentrated ammonia under pressure; (2) by reacting acrylontrile with a C1-7 alkyl formate in the presence of an alkali metal C1-7 alkoxide, alkylating the resulting alkali metal salt of an a -[(C1-7 alkoxy)-methyl]-b -hydroxy-acrylonitrile with a C1-7 alkylating agent and reacting the a -[(C1-7 alkoxy)-methyl]-b (C1-7 alkoxy)-acrylonitrile thus obtained with butyramidine.
GB34753/62A 1959-11-09 1960-05-06 Preparation of 4-amino-5-(lower alkoxy)-methyl-2-propyl-pyrimidines Expired GB953876A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US85152059A 1959-11-09 1959-11-09
US85884759A 1959-11-11 1959-11-11
US85916159A 1959-12-14 1959-12-14

Publications (1)

Publication Number Publication Date
GB953876A true GB953876A (en) 1964-04-02

Family

ID=27420358

Family Applications (2)

Application Number Title Priority Date Filing Date
GB34753/62A Expired GB953876A (en) 1959-11-09 1960-05-06 Preparation of 4-amino-5-(lower alkoxy)-methyl-2-propyl-pyrimidines
GB16121/60A Expired GB953875A (en) 1959-11-09 1960-05-06 New pyridinium compounds, a process for the manufacture thereof and compositions containing same

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB16121/60A Expired GB953875A (en) 1959-11-09 1960-05-06 New pyridinium compounds, a process for the manufacture thereof and compositions containing same

Country Status (7)

Country Link
BE (1) BE590665A (en)
CH (3) CH441337A (en)
DE (1) DE1216314B (en)
ES (1) ES258116A1 (en)
GB (2) GB953876A (en)
NL (1) NL251380A (en)
SE (3) SE309593B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4918191A (en) * 1988-09-02 1990-04-17 Basf Aktinegesellschaft Preparation of 2-n-propyl-4-amino-5-methoxymethyl-pyrimidine
CN116874536A (en) * 2023-07-11 2023-10-13 岳阳市金茂泰科技有限公司 Industrial production method of dicyclopentadiene zirconium dichloride

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2587262A (en) * 1952-02-26 Chs chzghjoh

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4918191A (en) * 1988-09-02 1990-04-17 Basf Aktinegesellschaft Preparation of 2-n-propyl-4-amino-5-methoxymethyl-pyrimidine
EP0358081A3 (en) * 1988-09-02 1990-05-09 BASF Aktiengesellschaft Process for the preparation of 2-n-propyl-4-amino-5-methoxy-methyl pyrimidine
CN116874536A (en) * 2023-07-11 2023-10-13 岳阳市金茂泰科技有限公司 Industrial production method of dicyclopentadiene zirconium dichloride

Also Published As

Publication number Publication date
DE1216314B (en) 1966-05-12
NL251380A (en)
SE311655B (en) 1969-06-23
SE319670B (en) 1970-01-19
SE309593B (en) 1969-03-31
ES258116A1 (en) 1960-12-01
CH441338A (en) 1967-08-15
CH441337A (en) 1967-08-15
CH401068A (en) 1965-10-31
GB953875A (en) 1964-04-02
BE590665A (en)

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