SU500759A3 - Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3- д / пиримидина - Google Patents
Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3- д / пиримидинаInfo
- Publication number
- SU500759A3 SU500759A3 SU1953843A SU1953843A SU500759A3 SU 500759 A3 SU500759 A3 SU 500759A3 SU 1953843 A SU1953843 A SU 1953843A SU 1953843 A SU1953843 A SU 1953843A SU 500759 A3 SU500759 A3 SU 500759A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- pyrimidine
- thieno
- furyl
- nitro
- nitric acid
- Prior art date
Links
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 23
- -1 5-nitro-2-furyl Chemical group 0.000 title description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 13
- 229910017604 nitric acid Inorganic materials 0.000 description 13
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OHMLBZKIUZTEOC-UHFFFAOYSA-N 2-aminothiophene-3-carboxylic acid Chemical class NC=1SC=CC=1C(O)=O OHMLBZKIUZTEOC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002594 sorbent Substances 0.000 description 2
- GLSFEIVUIPTZML-UHFFFAOYSA-N 2-(furan-2-yl)-N-propan-2-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound O1C(=CC=C1)C=1N=C(C2=C(N=1)SC=C2)NC(C)C GLSFEIVUIPTZML-UHFFFAOYSA-N 0.000 description 1
- WDTTYXVVVBLUFZ-UHFFFAOYSA-N 4-chloro-2-(furan-2-yl)thieno[2,3-d]pyrimidine Chemical compound N=1C=2SC=CC=2C(Cl)=NC=1C1=CC=CO1 WDTTYXVVVBLUFZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- XYAPAXXZIMTRSU-UHFFFAOYSA-N N-[2-[[2-(furan-2-yl)thieno[2,3-d]pyrimidin-4-yl]amino]ethyl]acetamide Chemical compound C(C)(=O)NCCNC=1C2=C(N=C(N=1)C=1OC=CC=1)SC=C2 XYAPAXXZIMTRSU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BOPMYCBIKFKLEI-UHFFFAOYSA-N n,n-dibutyl-2-(furan-2-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=2SC=CC=2C(N(CCCC)CCCC)=NC=1C1=CC=CO1 BOPMYCBIKFKLEI-UHFFFAOYSA-N 0.000 description 1
- KSSGFHFTFXROIJ-UHFFFAOYSA-N n-[2-[[2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidin-4-yl]amino]ethyl]acetamide Chemical compound N=1C=2SC=CC=2C(NCCNC(=O)C)=NC=1C1=CC=C([N+]([O-])=O)O1 KSSGFHFTFXROIJ-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117658 DE2117658A1 (de) | 1971-04-10 | 1971-04-10 | Neue 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 2,3-d eckige Klammer zu pyrimidine und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU500759A3 true SU500759A3 (ru) | 1976-01-25 |
Family
ID=5804484
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1953843A SU500759A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3- д / пиримидина |
| SU1955919A SU474142A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3-пиримидина |
| SU1953845A SU501673A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-(5-нитро-2-фурил)-тиено(2,3- ) пиримидина |
| SU1953844A SU509234A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидина |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1955919A SU474142A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3-пиримидина |
| SU1953845A SU501673A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-(5-нитро-2-фурил)-тиено(2,3- ) пиримидина |
| SU1953844A SU509234A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидина |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3830813A (cg-RX-API-DMAC7.html) |
| AT (4) | AT319255B (cg-RX-API-DMAC7.html) |
| AU (1) | AU467357B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE781899A (cg-RX-API-DMAC7.html) |
| BG (4) | BG20605A3 (cg-RX-API-DMAC7.html) |
| CA (1) | CA972370A (cg-RX-API-DMAC7.html) |
| CH (4) | CH567510A5 (cg-RX-API-DMAC7.html) |
| DD (1) | DD98683A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2117658A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK127854B (cg-RX-API-DMAC7.html) |
| ES (2) | ES401589A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2132839B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1384161A (cg-RX-API-DMAC7.html) |
| HU (1) | HU163362B (cg-RX-API-DMAC7.html) |
| IE (1) | IE36268B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL39173A (cg-RX-API-DMAC7.html) |
| NL (1) | NL7204782A (cg-RX-API-DMAC7.html) |
| NO (1) | NO129147B (cg-RX-API-DMAC7.html) |
| PH (1) | PH10479A (cg-RX-API-DMAC7.html) |
| PL (1) | PL83559B1 (cg-RX-API-DMAC7.html) |
| RO (5) | RO63034A (cg-RX-API-DMAC7.html) |
| SU (4) | SU500759A3 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA722415B (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001412A (en) * | 1972-02-28 | 1977-01-04 | Sumitomo Chemical Company, Limited | 1-Substituted-1,2-dihydrothieno[2,3-d]-pyrimidin-2-one derivatives |
| FI54312C (fi) * | 1972-05-09 | 1978-11-10 | Sumitomo Chemical Co | Foerfarande foer framstaellning av tieno-(2,3-d)pyrimidinderivat med avsoendring av urinsyra i urin utoekande |
| US4054656A (en) * | 1975-09-10 | 1977-10-18 | Mead Johnson & Company | Thieno[2,3-d]pyrimidine antiallergic agents |
| GB1570494A (en) * | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US7427623B2 (en) * | 2001-09-11 | 2008-09-23 | Smithkline Beecham Corporation | 4-Amino-2,3-disubstituted thieno[2,3-d]pyrimidines and pharmacetical compositions thereof |
-
1971
- 1971-04-10 DE DE19712117658 patent/DE2117658A1/de active Pending
-
1972
- 1972-04-05 US US00241414A patent/US3830813A/en not_active Expired - Lifetime
- 1972-04-05 PH PH13419A patent/PH10479A/en unknown
- 1972-04-07 NO NO01196/72*[A patent/NO129147B/no unknown
- 1972-04-07 AT AT951673A patent/AT319255B/de not_active IP Right Cessation
- 1972-04-07 DK DK170772AA patent/DK127854B/da unknown
- 1972-04-07 AT AT951773A patent/AT318633B/de not_active IP Right Cessation
- 1972-04-07 AT AT951573A patent/AT318632B/de not_active IP Right Cessation
- 1972-04-07 GB GB1621172A patent/GB1384161A/en not_active Expired
- 1972-04-07 CA CA139,148A patent/CA972370A/en not_active Expired
- 1972-04-07 AT AT301272A patent/AT318618B/de not_active IP Right Cessation
- 1972-04-07 DD DD162149A patent/DD98683A5/xx unknown
- 1972-04-08 BG BG021464A patent/BG20605A3/xx unknown
- 1972-04-08 BG BG20180A patent/BG20810A3/xx unknown
- 1972-04-08 BG BG021463A patent/BG19183A3/xx unknown
- 1972-04-08 PL PL1972154623A patent/PL83559B1/pl unknown
- 1972-04-08 RO RO7200077451A patent/RO63034A/ro unknown
- 1972-04-08 RO RO7200077448A patent/RO63014A/ro unknown
- 1972-04-08 RO RO7200077450A patent/RO63015A/ro unknown
- 1972-04-08 RO RO7200077449A patent/RO63033A/ro unknown
- 1972-04-08 ES ES401589A patent/ES401589A1/es not_active Expired
- 1972-04-08 RO RO7200070471A patent/RO62748A/ro unknown
- 1972-04-08 BG BG021462A patent/BG20604A3/xx unknown
- 1972-04-10 IE IE460/72A patent/IE36268B1/xx unknown
- 1972-04-10 CH CH870675A patent/CH567510A5/xx not_active IP Right Cessation
- 1972-04-10 CH CH870375A patent/CH575952A5/xx not_active IP Right Cessation
- 1972-04-10 CH CH524972A patent/CH575951A5/xx not_active IP Right Cessation
- 1972-04-10 HU HUTO871A patent/HU163362B/hu unknown
- 1972-04-10 ZA ZA722415A patent/ZA722415B/xx unknown
- 1972-04-10 CH CH870575A patent/CH583736A5/xx not_active IP Right Cessation
- 1972-04-10 AU AU40957/72A patent/AU467357B2/en not_active Expired
- 1972-04-10 FR FR7212539A patent/FR2132839B1/fr not_active Expired
- 1972-04-10 BE BE781899A patent/BE781899A/xx unknown
- 1972-04-10 IL IL39173A patent/IL39173A/xx unknown
- 1972-04-10 NL NL7204782A patent/NL7204782A/xx unknown
- 1972-10-11 ES ES407519A patent/ES407519A1/es not_active Expired
-
1973
- 1973-07-31 SU SU1953843A patent/SU500759A3/ru active
- 1973-07-31 SU SU1955919A patent/SU474142A3/ru active
- 1973-07-31 SU SU1953845A patent/SU501673A3/ru active
- 1973-07-31 SU SU1953844A patent/SU509234A3/ru active
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