GB1461184A - Process for the manufacture of 5-fluorocytosine - Google Patents
Process for the manufacture of 5-fluorocytosineInfo
- Publication number
- GB1461184A GB1461184A GB3901574A GB3901574A GB1461184A GB 1461184 A GB1461184 A GB 1461184A GB 3901574 A GB3901574 A GB 3901574A GB 3901574 A GB3901574 A GB 3901574A GB 1461184 A GB1461184 A GB 1461184A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethoxy
- fluorocytosine
- fluoropyrimidines
- prepared
- sept
- 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
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 title abstract 3
- 229960004413 flucytosine Drugs 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- UNPWKSQAHRVMMH-UHFFFAOYSA-N 2-ethoxy-5-fluoropyrimidin-4-amine Chemical compound CCOC1=NC=C(F)C(N)=N1 UNPWKSQAHRVMMH-UHFFFAOYSA-N 0.000 abstract 2
- XREDGJFKPWBNRQ-UHFFFAOYSA-N 2-ethoxy-5-fluoro-1h-pyrimidin-6-one Chemical compound CCOC1=NC=C(F)C(=O)N1 XREDGJFKPWBNRQ-UHFFFAOYSA-N 0.000 abstract 1
- DYBCJJAIMCCRDM-UHFFFAOYSA-N 2-ethoxy-5-fluoropyrimidine Chemical class CCOC1=NC=C(F)C=N1 DYBCJJAIMCCRDM-UHFFFAOYSA-N 0.000 abstract 1
- BUVSCQCSEWBHDI-UHFFFAOYSA-N 4-chloro-2-ethoxy-5-fluoropyrimidine Chemical class CCOC1=NC=C(F)C(Cl)=N1 BUVSCQCSEWBHDI-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-07 | 1973-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1461184A true GB1461184A (en) | 1977-01-13 |
Family
ID=4387383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3901574A Expired GB1461184A (en) | 1973-09-07 | 1974-09-06 | Process for the manufacture of 5-fluorocytosine |
Country Status (10)
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009094442A3 (en) * | 2008-01-22 | 2009-11-19 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives as fungicides |
| US8470839B2 (en) | 2009-08-07 | 2013-06-25 | Dow Agrosciences, Llc. | N1-acyl-5-fluoropyrimidinone derivatives |
| US8552020B2 (en) | 2009-08-07 | 2013-10-08 | Dow Agrosciences, Llc. | N1-substituted-5-fluoro-2-oxopyrimidinone-1(2H)-carboxamide derivatives |
| US8658660B2 (en) | 2011-08-17 | 2014-02-25 | Dow Agrosciences, Llc. | 5-fluoro-4-imino-3,4-dihydropyrimidin-2-(1H)-ones derivatives |
| US8916579B2 (en) | 2009-08-07 | 2014-12-23 | Dow Agrosciences, Llc. | 5-fluoropyrimidinone derivatives |
| US8921382B2 (en) | 2010-01-07 | 2014-12-30 | Dow Agrosciences, Llc. | Thiazolo[5,4-d] pyrimidines and their use as agrochemicals |
| US9006259B2 (en) | 2009-08-07 | 2015-04-14 | Dow Agrosciences Llc | N1-sulfonyl-5-fluoropyrimidinone derivatives |
| US9271497B2 (en) | 2012-12-28 | 2016-03-01 | Dow Agrosciences Llc | 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives |
| US9321734B2 (en) | 2012-12-28 | 2016-04-26 | Dow Agrosciences Llc | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives |
| US9526245B2 (en) | 2013-12-31 | 2016-12-27 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control in cereals |
| US9622474B2 (en) | 2012-12-28 | 2017-04-18 | Adama Makhteshim Ltd. | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives |
| US9642368B2 (en) | 2012-12-31 | 2017-05-09 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
| US9840476B2 (en) | 2013-12-31 | 2017-12-12 | Adama Makteshim Ltd. | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation |
Families Citing this family (1)
| 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 |
-
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
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2522430C2 (ru) * | 2008-01-22 | 2014-07-10 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | 5-фторпиримидиновые производные в качестве фунгицидов |
| JP2011510090A (ja) * | 2008-01-22 | 2011-03-31 | ダウ アグロサイエンシィズ エルエルシー | ５−フルオロピリミジン誘導体 |
| WO2009094442A3 (en) * | 2008-01-22 | 2009-11-19 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives as fungicides |
| US9204653B2 (en) | 2008-01-22 | 2015-12-08 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives |
| CN101977900B (zh) * | 2008-01-22 | 2013-11-27 | 陶氏益农公司 | 5-氟嘧啶衍生物 |
| US9174970B2 (en) * | 2008-01-22 | 2015-11-03 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives |
| US8552020B2 (en) | 2009-08-07 | 2013-10-08 | Dow Agrosciences, Llc. | N1-substituted-5-fluoro-2-oxopyrimidinone-1(2H)-carboxamide derivatives |
| US8916579B2 (en) | 2009-08-07 | 2014-12-23 | Dow Agrosciences, Llc. | 5-fluoropyrimidinone derivatives |
| US9000002B2 (en) | 2009-08-07 | 2015-04-07 | Dow Agrosciences Llc | N1-substituted-5-fluoro-2-oxopyrimidinone-1(2H)-carboxamide derivatives |
| US9006259B2 (en) | 2009-08-07 | 2015-04-14 | Dow Agrosciences Llc | N1-sulfonyl-5-fluoropyrimidinone derivatives |
| US9862686B2 (en) | 2009-08-07 | 2018-01-09 | Adama Makhteshim Ltd. | N1-sulfonyl-5-fluoropyrimidinone derivatives |
| US8470839B2 (en) | 2009-08-07 | 2013-06-25 | Dow Agrosciences, Llc. | N1-acyl-5-fluoropyrimidinone derivatives |
| US8921382B2 (en) | 2010-01-07 | 2014-12-30 | Dow Agrosciences, Llc. | Thiazolo[5,4-d] pyrimidines and their use as agrochemicals |
| US8658660B2 (en) | 2011-08-17 | 2014-02-25 | Dow Agrosciences, Llc. | 5-fluoro-4-imino-3,4-dihydropyrimidin-2-(1H)-ones derivatives |
| US9908855B2 (en) | 2012-12-28 | 2018-03-06 | Adama Makhteshim Ltd. | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives |
| US9840475B2 (en) | 2012-12-28 | 2017-12-12 | Adama Makhteshim Ltd. | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives |
| US9271497B2 (en) | 2012-12-28 | 2016-03-01 | Dow Agrosciences Llc | 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives |
| US9321734B2 (en) | 2012-12-28 | 2016-04-26 | Dow Agrosciences Llc | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives |
| US9622474B2 (en) | 2012-12-28 | 2017-04-18 | Adama Makhteshim Ltd. | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives |
| US9642368B2 (en) | 2012-12-31 | 2017-05-09 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
| US10059703B2 (en) | 2012-12-31 | 2018-08-28 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
| US10045533B2 (en) | 2013-12-31 | 2018-08-14 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US9850215B2 (en) | 2013-12-31 | 2017-12-26 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1 H)-one and processes for their preparation |
| US9538753B2 (en) | 2013-12-31 | 2017-01-10 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control in cereals |
| US9532570B2 (en) | 2013-12-31 | 2017-01-03 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control in cereals |
| US10045534B2 (en) | 2013-12-31 | 2018-08-14 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US9840476B2 (en) | 2013-12-31 | 2017-12-12 | Adama Makteshim Ltd. | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation |
| US10051862B2 (en) | 2013-12-31 | 2018-08-21 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US9526245B2 (en) | 2013-12-31 | 2016-12-27 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control in cereals |
| US10426167B2 (en) | 2013-12-31 | 2019-10-01 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US10426165B2 (en) | 2013-12-31 | 2019-10-01 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US10426166B2 (en) | 2013-12-31 | 2019-10-01 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control |
| US10919864B2 (en) | 2013-12-31 | 2021-02-16 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2436149C3 (de) | 1979-06-07 |
| NL7410730A (nl) | 1975-03-11 |
| FR2247457B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-31 |
| SU578873A3 (ru) | 1977-10-30 |
| DD114263A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-20 |
| JPS5050386A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-06 |
| FR2247457A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19920906 |