DE1795635C3 - 2,4-Diamino-5-benzyIpyrimidine - Google Patents
2,4-Diamino-5-benzyIpyrimidineInfo
- Publication number
- DE1795635C3 DE1795635C3 DE19671795635 DE1795635A DE1795635C3 DE 1795635 C3 DE1795635 C3 DE 1795635C3 DE 19671795635 DE19671795635 DE 19671795635 DE 1795635 A DE1795635 A DE 1795635A DE 1795635 C3 DE1795635 C3 DE 1795635C3
- Authority
- DE
- Germany
- Prior art keywords
- diamino
- pyrimidine
- dimethoxy
- reaction
- compound
- 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
Links
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HPOCGNHBIFZCAN-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 HPOCGNHBIFZCAN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- HWLAHKWVFFIJLY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dimethoxyphenol;hydrochloride Chemical compound Cl.COC1=CC(CN(C)C)=CC(OC)=C1O HWLAHKWVFFIJLY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 2
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- 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
- C07D239/50—Three 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB737666A GB1128234A (en) | 1966-02-19 | 1966-02-19 | 5-benzylpyrimidine derivatives and process for the preparation thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795635A1 DE1795635A1 (de) | 1972-10-19 |
| DE1795635B2 DE1795635B2 (de) | 1977-09-22 |
| DE1795635C3 true DE1795635C3 (de) | 1978-05-11 |
Family
ID=9831956
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967W0043385 Granted DE1720012B2 (de) | 1966-02-19 | 1967-02-17 | Verfahren zur herstellung von 2,4-diamino-5-(3,4,5-trimethoxybenzyl)- pyrimidin |
| DE19671795635 Expired DE1795635C3 (de) | 1966-02-19 | 1967-02-17 | 2,4-Diamino-5-benzyIpyrimidine |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967W0043385 Granted DE1720012B2 (de) | 1966-02-19 | 1967-02-17 | Verfahren zur herstellung von 2,4-diamino-5-(3,4,5-trimethoxybenzyl)- pyrimidin |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT275534B (enExample) |
| BE (1) | BE694244A (enExample) |
| CA (1) | CA977754A (enExample) |
| CH (2) | CH513179A (enExample) |
| DE (2) | DE1720012B2 (enExample) |
| DK (2) | DK120344B (enExample) |
| ES (1) | ES336945A1 (enExample) |
| FI (1) | FI49714C (enExample) |
| FR (1) | FR6595M (enExample) |
| GB (1) | GB1128234A (enExample) |
| GR (1) | GR33641B (enExample) |
| IL (1) | IL27424A (enExample) |
| MY (1) | MY7100226A (enExample) |
| NL (1) | NL146811B (enExample) |
| NO (1) | NO124601B (enExample) |
| SE (2) | SE390412B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789904A (fr) * | 1971-10-12 | 1973-04-10 | Wellcome Found | Procedes de synthese organique |
| PT69656A (en) * | 1978-05-24 | 1979-06-01 | Wellcome Found | Benzylpyrimidine compositions |
| DE2944145A1 (de) | 1979-11-02 | 1981-05-14 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von 2,4-diaminopyrimidin |
-
1966
- 1966-02-19 GB GB737666A patent/GB1128234A/en not_active Expired
-
1967
- 1967-02-13 GR GR670133641A patent/GR33641B/el unknown
- 1967-02-13 IL IL2742467A patent/IL27424A/xx unknown
- 1967-02-15 CA CA983,015A patent/CA977754A/en not_active Expired
- 1967-02-16 AT AT409368A patent/AT275534B/de active
- 1967-02-16 AT AT153867A patent/AT270653B/de active
- 1967-02-16 NO NO16687667A patent/NO124601B/no unknown
- 1967-02-17 NL NL6702397A patent/NL146811B/xx not_active IP Right Cessation
- 1967-02-17 BE BE694244D patent/BE694244A/xx not_active IP Right Cessation
- 1967-02-17 CH CH191468A patent/CH513179A/de not_active IP Right Cessation
- 1967-02-17 FI FI48067A patent/FI49714C/fi active
- 1967-02-17 ES ES336945A patent/ES336945A1/es not_active Expired
- 1967-02-17 DE DE1967W0043385 patent/DE1720012B2/de active Granted
- 1967-02-17 DE DE19671795635 patent/DE1795635C3/de not_active Expired
- 1967-02-17 CH CH237967A patent/CH511239A/de not_active IP Right Cessation
- 1967-02-20 DK DK91167A patent/DK120344B/da not_active IP Right Cessation
- 1967-02-20 SE SE796270A patent/SE390412B/xx unknown
- 1967-02-20 SE SE227867A patent/SE338998B/xx unknown
- 1967-05-16 FR FR106573A patent/FR6595M/fr not_active Expired
-
1971
- 1971-02-10 DK DK59371A patent/DK128247B/da not_active IP Right Cessation
- 1971-12-31 MY MY7100226A patent/MY7100226A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH513179A (de) | 1971-09-30 |
| BE694244A (enExample) | 1967-08-17 |
| NL146811B (nl) | 1975-08-15 |
| DE1795635A1 (de) | 1972-10-19 |
| MY7100226A (en) | 1971-12-31 |
| CH511239A (de) | 1971-08-15 |
| FI49714C (fi) | 1975-09-10 |
| ES336945A1 (es) | 1968-01-16 |
| DK128247B (da) | 1974-03-25 |
| DE1720012B2 (de) | 1977-06-08 |
| AT270653B (de) | 1969-05-12 |
| IL27424A (en) | 1971-02-25 |
| NL6702397A (enExample) | 1967-08-21 |
| NO124601B (enExample) | 1972-05-08 |
| GB1128234A (en) | 1968-09-25 |
| DE1720012A1 (de) | 1972-04-06 |
| FR6595M (enExample) | 1969-01-06 |
| FI49714B (enExample) | 1975-06-02 |
| SE390412B (sv) | 1976-12-20 |
| DE1795635B2 (de) | 1977-09-22 |
| GR33641B (el) | 1968-01-03 |
| AT275534B (de) | 1969-10-27 |
| CA977754A (en) | 1975-11-11 |
| DK120344B (da) | 1971-05-17 |
| SE338998B (enExample) | 1971-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. DR.JUR. DR.RER.NAT. MARX, L., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |