GB1461184A - Process for the manufacture of 5-fluorocytosine - Google Patents

Process for the manufacture of 5-fluorocytosine

Info

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
Application number
GB3901574A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1461184A publication Critical patent/GB1461184A/en
Expired legal-status Critical Current

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
    • C07D239/32—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

Abstract

1461184 5-Fluorocytosine; 2-ethoxy-5-fluoropyrimidines F HOFFMANN-LA ROCHE & CO AG 6 Sept 1974 [7 Sept 1973] 39015/74 Heading C2C 5 - Fluorocytosine is prepared by hydrolysis of a 2-ethoxy-4-amino-5-fluoropyrimidine of general formula The reaction is preferably effected using a strong mineral acid such as HCl in excess and converting to the free base by addition of NH 3 . 2 - Ethoxy - 4 - amino - 5 - fluoropyrimidines are prepared by treatment of the corresponding 4-chloro-derivative with NH 3 . 2 - Ethoxy - 4 - chloro - 5 - fluoropyrimidines are prepared by chlorinating a corresponding 2-ethoxy 5-fluoro-4(3H)-pyrimidinone in the 4-position.
GB3901574A 1973-09-07 1974-09-06 Process for the manufacture of 5-fluorocytosine Expired GB1461184A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1289573A CH579057A5 (en) 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)

Country Link
JP (1) JPS5050386A (en)
AT (1) AT331259B (en)
BE (1) BE819606A (en)
CH (1) CH579057A5 (en)
DD (1) DD114263A5 (en)
DE (1) DE2436149C3 (en)
FR (1) FR2247457B1 (en)
GB (1) GB1461184A (en)
NL (1) NL7410730A (en)
SU (1) SU578873A3 (en)

Cited By (13)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2522430C2 (en) * 2008-01-22 2014-07-10 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи 5-fluoropyrimidine derivatives as fungicides
JP2011510090A (en) * 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-Fluoropyrimidine derivatives
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 (en) * 2008-01-22 2013-11-27 陶氏益农公司 5-fluoro pyrimidine derivatives
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
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
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
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
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
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
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
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
DD114263A5 (en) 1975-07-20
ATA720874A (en) 1975-11-15
JPS5050386A (en) 1975-05-06
FR2247457B1 (en) 1976-10-22
FR2247457A1 (en) 1975-05-09
DE2436149A1 (en) 1975-03-27
NL7410730A (en) 1975-03-11
SU578873A3 (en) 1977-10-30
DE2436149B2 (en) 1978-10-12
AT331259B (en) 1976-08-10
BE819606A (en) 1975-03-06
CH579057A5 (en) 1976-08-31
DE2436149C3 (en) 1979-06-07

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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