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GB1409034A - Process for the manufacture of benzyl-pyrimidine derivatives - Google Patents

Process for the manufacture of benzyl-pyrimidine derivatives

Info

Publication number
GB1409034A
GB1409034A GB842074A GB842074A GB1409034A GB 1409034 A GB1409034 A GB 1409034A GB 842074 A GB842074 A GB 842074A GB 842074 A GB842074 A GB 842074A GB 1409034 A GB1409034 A GB 1409034A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
compounds
formula
benzyloxy
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
GB842074A
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 GB1409034A publication Critical patent/GB1409034A/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
    • C07D239/48—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
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

1409034 2,4-Diamino-pyrimidene derivatives F HOFFMANN-LA ROCHE & CO AG 25 Feb 1974 [26 Feb 1973] 8420/74 Heading C2C Compounds of Formula I wherein each of R 1 and R 2 independently represents a C 1-7 alkoxy group or R 1 and R 2 together represent a methylenedioxy group and R 3 represents hydrogen or a C 1-7 alkyl group and acid addition salts thereof are obtained by reacting together at 50‹-110‹ C. compounds of Formulµ II and III wherein R 4 represents halogen, C 1-7 alkoxy, benzyloxy or hydroxy, in the presence of an acid (e.g. H 3 PO 4 ), followed by neutralization when the free base of Formula I is required. Claimed per se are the novel starting materials of Formula IIIb wherein R 4 <SP>11</SP> represents halogen, C 1-7 alkoxy or benzyloxy. Compounds of Formula III wherein R 4 represents C 1-7 alkoxy or benzyloxy are obtained by (i) reacting a #-(C 1-7 alkoxy or benzyloxy)- propionitrile with methyl formate in the presence of an alkali metal alcoholate or an alkali metal benzyloxide, preferably under CO pressure and (ii) reacting the thus formed mixture of cis- and trans-α-methoxymethylene-#-(C 1-7 alkoxy or benzyloxy)-propionitrile with guanidine or the carbonate thereof. The compounds of Formula III wherein R 4 represents halogen are prepared by reacting a compound wherein R 4 is C 1-7 alkoxy with a hydrohalic acid in a solvent. Examples prepare 2,4 - diamino - 5(4,5 - dimethoxy - 2 - methyl or 2 - n - propyl - benzyl)- pyrimidines and 2,4-diamino-5(3,4-dimethoxybenzyl)pyrimidine. Compounds of Formula IIIb prepared or otherwise specified are those wherein R 4 <SP>11</SP> is CH 3 O-, C 2 H 5 O-, F, Cl or Br. The compounds of Formula I are potentiators for sulphoriamides.
GB842074A 1973-02-26 1974-02-25 Process for the manufacture of benzyl-pyrimidine derivatives Expired GB1409034A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US33609473A 1973-02-26 1973-02-26

Publications (1)

Publication Number Publication Date
GB1409034A true GB1409034A (en) 1975-10-08

Family

ID=23314538

Family Applications (1)

Application Number Title Priority Date Filing Date
GB842074A Expired GB1409034A (en) 1973-02-26 1974-02-25 Process for the manufacture of benzyl-pyrimidine derivatives

Country Status (8)

Country Link
JP (1) JPS5939429B2 (en)
AT (1) AT338272B (en)
BE (1) BE811504A (en)
CH (1) CH592066A5 (en)
DE (1) DE2405683A1 (en)
FR (1) FR2219162B1 (en)
GB (1) GB1409034A (en)
NL (1) NL180104C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4723006A (en) * 1982-10-15 1988-02-02 Ciba-Geigy Corporation Process for 4,6-di-substituted 2-aminopyrimidines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2516081B1 (en) * 1981-11-09 1987-05-29 Wellcome Found SYNTHESIS OF BENZYLPYRIMIDINES AND INTERMEDIATES FOR THE SYNTHESIS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD94818A5 (en) * 1970-10-22 1973-01-05
BE789904A (en) * 1971-10-12 1973-04-10 Wellcome Found ORGANIC SYNTHESIS PROCESSES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4723006A (en) * 1982-10-15 1988-02-02 Ciba-Geigy Corporation Process for 4,6-di-substituted 2-aminopyrimidines

Also Published As

Publication number Publication date
NL7401764A (en) 1974-08-28
DE2405683A1 (en) 1974-09-05
FR2219162A1 (en) 1974-09-20
JPS5939429B2 (en) 1984-09-22
BE811504A (en) 1974-08-26
JPS49117478A (en) 1974-11-09
FR2219162B1 (en) 1977-09-16
ATA151974A (en) 1976-12-15
CH592066A5 (en) 1977-10-14
NL180104C (en) 1987-01-02
NL180104B (en) 1986-08-01
AT338272B (en) 1977-08-10

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Legal Events

Date Code Title Description
PS Patent sealed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
429A Application made for amendment of specification (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SP Amendment (slips) printed
PE20 Patent expired after termination of 20 years

Effective date: 19940224