IL43658A - Manufacture of benzyl-pyrimidines - Google Patents

Manufacture of benzyl-pyrimidines

Info

Publication number
IL43658A
IL43658A IL43658A IL4365873A IL43658A IL 43658 A IL43658 A IL 43658A IL 43658 A IL43658 A IL 43658A IL 4365873 A IL4365873 A IL 4365873A IL 43658 A IL43658 A IL 43658A
Authority
IL
Israel
Prior art keywords
hydrogen
formula
lower alkoxy
lower alkyl
alkoxy
Prior art date
Application number
IL43658A
Other versions
IL43658A0 (en
Original Assignee
Sparamedica 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 Sparamedica Ag filed Critical Sparamedica Ag
Publication of IL43658A0 publication Critical patent/IL43658A0/en
Publication of IL43658A publication Critical patent/IL43658A/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
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

Landscapes

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

Abstract

1411170 Benzyl-pyrimidines FHOFFMANNLA ROCHE & CO AG 20 Dec 1973 [21 Dec 1972] 59104/73 Heading C2C [Also in Division A5] Benzylpyrimidines of Formula I in which R 1 =H or C 1-7 alkyl, R 2 =H or C 1-7 alkoxy, R 3 =C 1-7 alkyl or C 1-7 alkoxy and R 4 =H or C 1-7 alkoxy or R 2 and R 3 together = methylenedioxy, are prepared by reacting a compound of Formula II in which R = C 1-7 alkyl, with an alkali metal alkoxide in an aprotic dipolar solvent (e.g. dimethylformamide, dimethyl sulphoxide or hexamethylphosphoramide) and an alkanol of formula ROH, and treating the resulting mixture with guanidine. Compounds I potentiate the antibacterial of sulpha drugs. Reference has been directed by the Comptroller to Specification 1,133,766. [GB1411170A]

Claims (6)

Having now particularly described and ascertained the nature of our said invention and in what manner the same is to be performed, we declare that what we claim is:
1. A process for the preparation of 2,4-diamino-pyrimidines of the formula wherein is hydrogen or lower alkyl; R2 is hydrogen or lower alkoxy; R^ is lower alkoxy or lower alkyl; R^ is hydrogen or lower alkoxy; and Rg and R^, when taken together, are methylenedioxy , which comprises treating the correspondingly substituted a-alkoxymethylcinnamonitrile of the formula wherein R^, R^t ^ and R^ are as previously defined and R is lower alkyl, liit an alkali metal alkoxide in an aprotic dipolar solvent and an alkanol of the formula ROH, wherein R is as previously defined and treating the resulting reaction mixture with guanidine .
2. A process in accordance with claim 1, wherein the aprotic dipolar solvent is dimethylformamide , dimethylsulfoxide or hexamethylphosphoramide .
3. A process in accordance with claim 2, wherein the guanidine is generated from guanidine carbonate.
4. A process in accordance with claim 3, wherein the reaction is carried out at a temperature in the range of from about 60° to about 140°C.
5. Process for the preparation of 2 ,4-diamino-pyrimi as hereinbefore particularly described, especially with reference to the foregoing Examples.
6. Compounds of the formula wherein R^ is hydrogen or lower alkyl; is hydrogen or lower alkoxy; R^ is lower alkoxy or lower alkyl; R^ is hydrogen or lower alkoxy; and R2 and R^, when taken together, are methylenedioxy , whenever prepared according to any one of claims .1-5 or by an obvious chemical equivalent thereof.
IL43658A 1972-12-21 1973-11-20 Manufacture of benzyl-pyrimidines IL43658A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31750072A 1972-12-21 1972-12-21

Publications (2)

Publication Number Publication Date
IL43658A0 IL43658A0 (en) 1974-03-14
IL43658A true IL43658A (en) 1976-12-31

Family

ID=23233931

Family Applications (1)

Application Number Title Priority Date Filing Date
IL43658A IL43658A (en) 1972-12-21 1973-11-20 Manufacture of benzyl-pyrimidines

Country Status (15)

Country Link
JP (1) JPS4988886A (en)
AT (1) AT339315B (en)
AU (1) AU476694B2 (en)
BE (1) BE808870A (en)
CA (1) CA986937A (en)
CH (1) CH592065A5 (en)
DE (1) DE2363533A1 (en)
DK (1) DK135531B (en)
FR (1) FR2211463B1 (en)
GB (1) GB1411170A (en)
HU (1) HU169082B (en)
IL (1) IL43658A (en)
NL (1) NL7317484A (en)
PH (1) PH12708A (en)
ZA (1) ZA738760B (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL122146C (en) * 1960-09-02
US3485840A (en) * 1964-11-12 1969-12-23 Hoffmann La Roche 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes
GB1407971A (en) * 1971-04-16 1975-10-01 Wellcome Found 2,4-diamino -4-3,4,5-triethoxybenzyl pyrimidine and methods of preparation therefor
BE792096A (en) * 1971-12-01 1973-05-30 Hoffmann La Roche NEW BENZYLPYRIMIDINES
BE795023A (en) * 1972-02-07 1973-08-06 Hoffmann La Roche NEW BENZYLPYRIMIDINES

Also Published As

Publication number Publication date
FR2211463A1 (en) 1974-07-19
IL43658A0 (en) 1974-03-14
BE808870A (en) 1974-06-20
ZA738760B (en) 1974-08-28
DK135531C (en) 1977-10-10
PH12708A (en) 1979-07-20
ATA1070773A (en) 1977-02-15
AT339315B (en) 1977-10-10
CH592065A5 (en) 1977-10-14
DE2363533A1 (en) 1974-06-27
CA986937A (en) 1976-04-06
GB1411170A (en) 1975-10-29
JPS4988886A (en) 1974-08-24
DK135531B (en) 1977-05-16
AU476694B2 (en) 1976-09-30
HU169082B (en) 1976-09-28
NL7317484A (en) 1974-06-25
FR2211463B1 (en) 1979-05-11
AU6275573A (en) 1975-05-22

Similar Documents

Publication Publication Date Title
GB1476215A (en) Dibenzoxepin derivatives process for the preparation thereof and pharmaceutical compositions containing them
IL43658A (en) Manufacture of benzyl-pyrimidines
GB1341895A (en) Oximino malonitrile compounds
GB1177868A (en) alpha,omega-Bis(Fluoroperhaloisopropoxy)-Perfluoroalkanes
JPS5524125A (en) Preparation of substituted diphenyl ether
GB1293336A (en) PRODUCTION OF 2,3-DIHYDRO-p DITHIINES AND THEIR SULPHOXIDES AND SULPHONES
GB1378913A (en) Process for the production of ketones
GB1283452A (en) Substituted 1,3-dialkylpyrrolidines and processes for their production
GB1250820A (en)
GB1449967A (en) Thiolphosphoric acid esters having pesticidal properties
GB1389691A (en) Thiazolotriazolylphosphorothioates and the preparation and uses thereof
GB1307191A (en) N-trihalomethanesulphenyl-n-methyl-carbamates process for their production and their use as pesticides
GB1240780A (en) Phosphoroamidothioate esters having herbicidal activity
GB1229148A (en)
GB1318386A (en) Phosphate and thiophosphate esters having insecticidal and acaricidal properties
Geevers et al. Reaction of N-chloro formimidoyl chlorides with disulfides
ES348007A1 (en) Thio-phosphoric (-phosphonic) and dithiophosphoric (-phosphonic) acid esters
GB1383983A (en) Pesticidal 2-dialkylamino-1,3-bis-alkoxyalkylthio propanes
GB956335A (en) Aliphatic ethers of hydroxymethylated diaryl oxides
GB1311773A (en) Phosphorothiolates and processes for preparing them
GB1132097A (en) Esters of thiophosphoric acid and pesticidal compositions containing them
GB1420768A (en) 8-hydroxy quinoline derivatives process for preparing same and pharmaceutical compositions containing siad compounds
JPS5683428A (en) Preparation of 2-substituted resorcinol
GB889715A (en) Process for the production of substituted triazines
Crampton et al. Intermediates in aromatic nucleophilic substitution reactions: Meisenheimer complexes from 1-chloro-2, 6-dinitro-4-X-benzenes