IE821520L - Preparation of 2, 4-diamino-5-(3',4'-5'-trimethoxy-benzyl)¹pyrimidine - Google Patents

Preparation of 2, 4-diamino-5-(3',4'-5'-trimethoxy-benzyl)¹pyrimidine

Info

Publication number
IE821520L
IE821520L IE821520A IE152082A IE821520L IE 821520 L IE821520 L IE 821520L IE 821520 A IE821520 A IE 821520A IE 152082 A IE152082 A IE 152082A IE 821520 L IE821520 L IE 821520L
Authority
IE
Ireland
Prior art keywords
general formula
compound
trimethoxy
image
reacting
Prior art date
Application number
IE821520A
Other versions
IE53466B1 (en
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
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 Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar
Publication of IE821520L publication Critical patent/IE821520L/en
Publication of IE53466B1 publication Critical patent/IE53466B1/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

Landscapes

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

Abstract

The invention relates to an improved process for the preparation of 2,4-diamino-5-(3',4',5'-trimethoxy-benzyl)-pyrimidine of the general formula I <IMAGE> by reacting a compound of the general formula II <IMAGE> (wherein R is an alkyl group having 1-4 carbon atoms) with guanidine, which comprises preparing the said compound of the general formula II by reacting alpha -(3,4,5-trimethoxy-benzal)- beta -methoxy-propionitrile of the formula III <IMAGE> with ethylene glycol monoalkylether of the general formula IV HO-CH2-CH2-OR (IV> (wherein R as as stated above) in the presence of an alkali metal alkoxide at a temperature between 60 DEG and 90 DEG and reacting the compound of the general formula II thus obtained - if desired without isolation - with guanidine in the presence of an alkanol having 4-8 carbon atoms. The advantage of the process is that it is economical and can be carried out with high yields even on industrial scale and provides a product of high purity. The compound of the formula I obtained is a known chemotherapeutical drug. [GB2104508A]
IE1520/82A 1981-06-26 1982-06-25 Improved process for the preparation of 2,4-diamino-5-(3',4',5'-trimethoxy-benzyl)-pyrimidine IE53466B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU811869A HU187370B (en) 1981-06-26 1981-06-26 Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine

Publications (2)

Publication Number Publication Date
IE821520L true IE821520L (en) 1982-12-26
IE53466B1 IE53466B1 (en) 1988-11-23

Family

ID=10956594

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1520/82A IE53466B1 (en) 1981-06-26 1982-06-25 Improved process for the preparation of 2,4-diamino-5-(3',4',5'-trimethoxy-benzyl)-pyrimidine

Country Status (21)

Country Link
JP (1) JPS5838266A (en)
AT (1) AT387961B (en)
AU (1) AU547823B2 (en)
BE (1) BE893611A (en)
CA (1) CA1174679A (en)
CH (1) CH648834A5 (en)
CS (1) CS244908B2 (en)
DD (1) DD202703A5 (en)
DK (1) DK155434C (en)
ES (1) ES513482A0 (en)
FI (1) FI76790C (en)
FR (1) FR2508450B1 (en)
GB (1) GB2104508B (en)
GR (1) GR76159B (en)
HU (1) HU187370B (en)
IE (1) IE53466B1 (en)
IL (1) IL66132A (en)
IT (1) IT1190889B (en)
SE (1) SE451133B (en)
SU (1) SU1145929A3 (en)
YU (1) YU42774B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2602507B1 (en) * 1986-08-08 1989-06-09 Sanofi Pharma PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-BENZYL-5 PYRIMIDINES

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB743221A (en) * 1953-05-26 1956-01-11 Wellcome Found Improvements in or relating to the manufacture of acrylonitriles
DE1303727B (en) * 1959-09-03 1976-02-05 Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London Alpha-arylidene-substituted propioni-iriles
NL122146C (en) * 1960-09-02
US4033962A (en) * 1975-06-26 1977-07-05 Hoffman-La Roche Inc. 2,4-Diamino-pyrimidine derivatives and processes
DE2635765C3 (en) * 1976-08-09 1979-02-08 Ludwig Heumann & Co Gmbh, 8500 Nuernberg Process for the preparation of 2,4-EMamino-5- (3 ', 4'r5'-trimethoxybenzyl) -pyrimidine
US4115650A (en) * 1976-11-17 1978-09-19 Hoffmann-La Roche Inc. Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines
DE2730467A1 (en) * 1977-07-06 1979-01-18 Basf Ag BENZYLPYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AND MEDICINAL PRODUCTS CONTAINING THE SAME

Also Published As

Publication number Publication date
CS471782A2 (en) 1985-09-17
AU547823B2 (en) 1985-11-07
IT8222035A0 (en) 1982-06-24
AT387961B (en) 1989-04-10
DK288082A (en) 1982-12-27
GR76159B (en) 1984-08-03
AU8534682A (en) 1983-01-06
SU1145929A3 (en) 1985-03-15
GB2104508A (en) 1983-03-09
FI76790C (en) 1988-12-12
CS244908B2 (en) 1986-08-14
SE8203914L (en) 1982-12-27
YU138582A (en) 1984-10-31
JPS5838266A (en) 1983-03-05
FR2508450A1 (en) 1982-12-31
BE893611A (en) 1982-12-23
CH648834A5 (en) 1985-04-15
FI76790B (en) 1988-08-31
CA1174679A (en) 1984-09-18
SE451133B (en) 1987-09-07
IE53466B1 (en) 1988-11-23
ES8304949A1 (en) 1983-04-01
FR2508450B1 (en) 1986-01-03
FI822268A0 (en) 1982-06-24
YU42774B (en) 1988-12-31
ATA244982A (en) 1988-09-15
FI822268L (en) 1982-12-27
DD202703A5 (en) 1983-09-28
GB2104508B (en) 1985-01-16
IT1190889B (en) 1988-02-24
IL66132A0 (en) 1982-09-30
SE8203914D0 (en) 1982-06-23
IL66132A (en) 1985-04-30
HU187370B (en) 1985-12-28
ES513482A0 (en) 1983-04-01
DK155434C (en) 1989-09-18
DK155434B (en) 1989-04-10

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Legal Events

Date Code Title Description
MM4A Patent lapsed