SU578873A3 - Способ получени 5-фторцитозина - Google Patents
Способ получени 5-фторцитозинаInfo
- Publication number
- SU578873A3 SU578873A3 SU7402057486A SU2057486A SU578873A3 SU 578873 A3 SU578873 A3 SU 578873A3 SU 7402057486 A SU7402057486 A SU 7402057486A SU 2057486 A SU2057486 A SU 2057486A SU 578873 A3 SU578873 A3 SU 578873A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- temperature
- ethoxy
- water
- ammonia
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- -1 2-ethoxy Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 3
- 229960004413 flucytosine Drugs 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BZNJWQYNUWZVBR-UHFFFAOYSA-N Cl(=O)(=O)[P] Chemical compound Cl(=O)(=O)[P] BZNJWQYNUWZVBR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SLQAJWTZUXJPNY-UHFFFAOYSA-N 2-chloro-5-fluoropyrimidin-4-amine Chemical compound NC1=NC(Cl)=NC=C1F SLQAJWTZUXJPNY-UHFFFAOYSA-N 0.000 description 1
- BUVSCQCSEWBHDI-UHFFFAOYSA-N 4-chloro-2-ethoxy-5-fluoropyrimidine Chemical compound CCOC1=NC=C(F)C(Cl)=N1 BUVSCQCSEWBHDI-UHFFFAOYSA-N 0.000 description 1
- PKZMNMQCFNJXEH-UHFFFAOYSA-N 5-fluoropyrimidin-4-amine Chemical compound NC1=NC=NC=C1F PKZMNMQCFNJXEH-UHFFFAOYSA-N 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1289573A CH579057A5 (OSRAM) | 1973-09-07 | 1973-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU578873A3 true SU578873A3 (ru) | 1977-10-30 |
Family
ID=4387383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402057486A SU578873A3 (ru) | 1973-09-07 | 1974-09-06 | Способ получени 5-фторцитозина |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5050386A (OSRAM) |
| AT (1) | AT331259B (OSRAM) |
| BE (1) | BE819606A (OSRAM) |
| CH (1) | CH579057A5 (OSRAM) |
| DD (1) | DD114263A5 (OSRAM) |
| DE (1) | DE2436149C3 (OSRAM) |
| FR (1) | FR2247457B1 (OSRAM) |
| GB (1) | GB1461184A (OSRAM) |
| NL (1) | NL7410730A (OSRAM) |
| SU (1) | SU578873A3 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080455A (en) * | 1975-12-16 | 1978-03-21 | Taisho Pharmaceutical Company Limited | 5-Fluoropyrimidin-4-one compositions |
| EP2562161A1 (en) * | 2008-01-22 | 2013-02-27 | Dow AgroSciences LLC | 5-fluoro pyrimidine derivatives as fungicides |
| UA112284C2 (uk) | 2009-08-07 | 2016-08-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні 5-фторпіримідинону |
| UA107671C2 (en) | 2009-08-07 | 2015-02-10 | Dow Agrosciences Llc | N1-substityted-5-fluoro-2-oxopyrimidinone-1(2h)-carboxamide derivatives |
| IN2012DN00692A (OSRAM) | 2009-08-07 | 2015-06-19 | Dow Agroscience Llc | |
| UA106889C2 (uk) | 2009-08-07 | 2014-10-27 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні n1-ацил-5-фторпіримідинону |
| IN2012DN06323A (OSRAM) | 2010-01-07 | 2015-10-02 | Dow Agrosciences Llc | |
| UA113062C2 (xx) | 2011-08-17 | 2016-12-12 | Похідні 5-фтор-4-іміно-3-(заміщеного)-3,4-дигідропіримідин-2(1h)ону | |
| HUE047711T2 (hu) | 2012-12-28 | 2020-05-28 | Adama Makhteshim Ltd | N-(szubsztituált)-5-fluor-4-imino-3-metil-2-oxo-3,4-dihidropirimidin-1(2H)-karboxilát származékok |
| EP2945635A4 (en) | 2012-12-28 | 2016-05-25 | Dow Agrosciences Llc | 1- (BENZOYL-SUBSTITUTED) -5-FLUORO-4-IMINO-3-METHYL-3,4-DIHYDROPYRIMIDIN-2 (1H) -ONE DERIVATIVES |
| KR20150100869A (ko) | 2012-12-28 | 2015-09-02 | 다우 아그로사이언시즈 엘엘씨 | N-(치환된)-5-플루오로-4-이미노-3-메틸-2-옥소-3,4-디히드로피리미딘-1(2h)-카르복스아미드 유도체 |
| AU2013370494B2 (en) | 2012-12-31 | 2017-08-17 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
| AU2014373850A1 (en) | 2013-12-31 | 2016-08-11 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions for fungal control |
| MX375727B (es) | 2013-12-31 | 2025-03-06 | Adama Makhteshim Ltd | 5-fluor-4-imino-3-(alquil/alquilo sustituido)-1-(arilsulfonil)-3,4-dihidropirimidin-2(1h)-ona y los procesos para su preparacion. |
-
1973
- 1973-09-07 CH CH1289573A patent/CH579057A5/xx not_active IP Right Cessation
-
1974
- 1974-07-26 DE DE19742436149 patent/DE2436149C3/de not_active Expired
- 1974-08-09 NL NL7410730A patent/NL7410730A/xx unknown
- 1974-09-05 JP JP10142674A patent/JPS5050386A/ja active Pending
- 1974-09-05 DD DD18093474A patent/DD114263A5/xx unknown
- 1974-09-05 FR FR7430135A patent/FR2247457B1/fr not_active Expired
- 1974-09-06 SU SU7402057486A patent/SU578873A3/ru active
- 1974-09-06 GB GB3901574A patent/GB1461184A/en not_active Expired
- 1974-09-06 BE BE148257A patent/BE819606A/xx not_active IP Right Cessation
- 1974-09-06 AT AT720874A patent/AT331259B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2436149C3 (de) | 1979-06-07 |
| NL7410730A (nl) | 1975-03-11 |
| FR2247457B1 (OSRAM) | 1976-10-22 |
| DE2436149A1 (de) | 1975-03-27 |
| AT331259B (de) | 1976-08-10 |
| DE2436149B2 (de) | 1978-10-12 |
| BE819606A (fr) | 1975-03-06 |
| ATA720874A (de) | 1975-11-15 |
| CH579057A5 (OSRAM) | 1976-08-31 |
| GB1461184A (en) | 1977-01-13 |
| DD114263A5 (OSRAM) | 1975-07-20 |
| JPS5050386A (OSRAM) | 1975-05-06 |
| FR2247457A1 (OSRAM) | 1975-05-09 |
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