IL38276A - Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines - Google Patents

Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines

Info

Publication number
IL38276A
IL38276A IL38276A IL3827671A IL38276A IL 38276 A IL38276 A IL 38276A IL 38276 A IL38276 A IL 38276A IL 3827671 A IL3827671 A IL 3827671A IL 38276 A IL38276 A IL 38276A
Authority
IL
Israel
Prior art keywords
general formula
compound
process according
stand
yield
Prior art date
Application number
IL38276A
Other versions
IL38276A0 (en
Original Assignee
Plantex Ltd
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
Priority to BE792122D priority Critical patent/BE792122A/en
Application filed by Plantex Ltd filed Critical Plantex Ltd
Priority to IL38276A priority patent/IL38276A/en
Publication of IL38276A0 publication Critical patent/IL38276A0/en
Priority to IE1597/72A priority patent/IE37186B1/en
Priority to AT1008872A priority patent/AT331249B/en
Priority to NO4340/72A priority patent/NO136195C/en
Priority to CA157,703A priority patent/CA989840A/en
Priority to SE7215519A priority patent/SE407061B/en
Priority to DE19722258238 priority patent/DE2258238A1/en
Priority to CH1731872A priority patent/CH584692A5/xx
Priority to ZA728428A priority patent/ZA728428B/en
Priority to AU49357/72A priority patent/AU476925B2/en
Priority to NL7216163A priority patent/NL7216163A/xx
Priority to OA54766A priority patent/OA04279A/en
Priority to DK598972A priority patent/DK132703C/en
Priority to GB5559772A priority patent/GB1406307A/en
Priority to SE7513881A priority patent/SE7513881L/en
Priority to HK456/76*UA priority patent/HK45676A/en
Priority to KE2660A priority patent/KE2660A/en
Publication of IL38276A publication Critical patent/IL38276A/en

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
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms

Landscapes

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

Abstract

Cpds. of formula (I) where R1 and R2 = H, halogen, lower alkyl, alkoxy; R3 and R4 = lower alkoxy; are prepd. by condensing a cpd. (II) in the presence of a basic condensing agent, with a cpd. (III) NC-CH2-COOR" where R" = lower alkyl; to give a cpd. (IV) which is catalytically hydrogenated to (V) this is reacted with guanidine to give (VI) which is reacted with POCl to form (VII) which is catalytically hydrogenated to give (I), (I) have antibacterial act. and are mainly used in combination with sulphonamides such as sulphamethoxazole or sulphaquinoxalin. [DE2258238A1]

Claims (1)

1. A process for the preparation of of general ormula I in and stand for the same or different lower alkyl lover alkoxy and stand for the or different lower alkoxy wherein an aldehyde of general formula in which and have the meaning in formula is reacted in the presence of a suitable basic catalyet with c anoacetio ester of general XI in which stands for an alkyl group to yield a compound of general formula the compound of general formula is hydrogenated with a suitable catalyst in a suitable inert solvent to yield a compound of general formula XIII in which have the meaning as the compound of general formula without a solvent or in the presence of a suitable reacted with to yield a compound of general formula XIV in which and have the ease meaning as above the compound of general formula XIV reacted with and a small amount of phosphorus ox chloride phosphorus pentachloride to yield a compound of general XV 4 in which and have the same meaning as and 16 the compound of general formula is hydrogenated catalytlcally with a suitable in a suitable solvent to yield a compound of general formula A process according to wherein reaction to are performed one after another without isolation of a compound of general formula or A process according to Claim 1 or wherein the basic catalyst a metal alkoxide in reaction step sodium or potassium a secondary A process accordin to any of 1 to wherein reaction step performed in a suitable inert an alcohol or an A process according to any of Claims 1 to wherein the catalyst is palladised charcoal and the inert solvent is selected among ethyl an alcohol and an A process according to any of Claims 1 to wherein the condensatio with is performed an alcoholic A process according to any of Claims 1 to wherein the formulae stands for hydrogen and and stand for methoxy groups and the compound of forraula X obtained is A process for the preparation of benzyl pyrlmidinee of general formula I as defined in Claim substantially as hereinbefore described with reference to the pyrlmidlnes of general formula X as defined whenever obtained by the process according to any of 17 Compounds of general formula in which and for the same or different lower lower and stand for the same or di ferent lover group and stand for chlorine or for a hydroxy For the Yitzhak Hess insufficientOCRQuality
IL38276A 1971-12-01 1971-12-01 Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines IL38276A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BE792122D BE792122A (en) 1971-12-01 BENZYL-PYRIMIDINES PREPARATION PROCESS
IL38276A IL38276A (en) 1971-12-01 1971-12-01 Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines
IE1597/72A IE37186B1 (en) 1971-12-01 1972-11-20 Improvements in and relating to the production of benzyl-pyrimidines
AT1008872A AT331249B (en) 1971-12-01 1972-11-27 PROCESS FOR THE PREPARATION OF 5-BENZYLPYRIMIDINES
NO4340/72A NO136195C (en) 1971-12-01 1972-11-27 PROCEDURES FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES.
SE7215519A SE407061B (en) 1971-12-01 1972-11-28 PROCEDURE FOR THE PREPARATION OF BENZYLPYRIMIDINES
CH1731872A CH584692A5 (en) 1971-12-01 1972-11-28
AU49357/72A AU476925B2 (en) 1971-12-01 1972-11-28 A process forthe preparation of benzylpyrimidines
DE19722258238 DE2258238A1 (en) 1971-12-01 1972-11-28 5-Benzylpyrimidines prepn - from benzaldehyde and cyanoacetic acid ester via 2,4-diamino-5-benzyl-6-hydroxypyrimidine
CA157,703A CA989840A (en) 1971-12-01 1972-11-28 Process for the preparation of benzylpyrimidines
ZA728428A ZA728428B (en) 1971-12-01 1972-11-28 A process for the preparation of benzylpyrimidines
NL7216163A NL7216163A (en) 1971-12-01 1972-11-29
OA54766A OA04279A (en) 1971-12-01 1972-11-29 Process for the preparation of benzyl-pyrimidines.
DK598972A DK132703C (en) 1971-12-01 1972-11-30 PROCEDURE FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES
GB5559772A GB1406307A (en) 1971-12-01 1972-12-01 Production of benzylpyrimidines
SE7513881A SE7513881L (en) 1971-12-01 1975-12-09 INTERMEDIATE PRODUCTS INTENDED FOR THE PREPARATION OF ANTIBACTERIAL BENZYLPYRIMIDINES
HK456/76*UA HK45676A (en) 1971-12-01 1976-07-15 Improvements in and relating to the production of benzylpyrimidines
KE2660A KE2660A (en) 1971-12-01 1976-09-15 Improvements in and relating to the production of benzylpyrimidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IL38276A IL38276A (en) 1971-12-01 1971-12-01 Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines

Publications (2)

Publication Number Publication Date
IL38276A0 IL38276A0 (en) 1972-02-29
IL38276A true IL38276A (en) 1976-09-30

Family

ID=11046229

Family Applications (1)

Application Number Title Priority Date Filing Date
IL38276A IL38276A (en) 1971-12-01 1971-12-01 Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines

Country Status (8)

Country Link
AT (1) AT331249B (en)
AU (1) AU476925B2 (en)
CA (1) CA989840A (en)
CH (1) CH584692A5 (en)
DE (1) DE2258238A1 (en)
IL (1) IL38276A (en)
NL (1) NL7216163A (en)
ZA (1) ZA728428B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5025575A (en) * 1973-07-03 1975-03-18
FR2283129A1 (en) * 1974-03-01 1976-03-26 Wellcome Found 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs
GR71725B (en) * 1977-11-10 1983-06-22 Hoffmann La Roche
CN105294574B (en) * 2015-11-25 2018-06-29 湖南湘易康制药有限公司 A kind of synthetic method of trimethoprim

Also Published As

Publication number Publication date
IL38276A0 (en) 1972-02-29
CA989840A (en) 1976-05-25
AT331249B (en) 1976-08-10
AU476925B2 (en) 1976-10-07
ZA728428B (en) 1973-10-31
AU4935772A (en) 1974-05-30
CH584692A5 (en) 1977-02-15
DE2258238A1 (en) 1973-06-07
NL7216163A (en) 1973-06-05
ATA1008872A (en) 1975-11-15

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