GB1174165A - Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position - Google Patents

Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position

Info

Publication number
GB1174165A
GB1174165A GB1792667A GB1792667A GB1174165A GB 1174165 A GB1174165 A GB 1174165A GB 1792667 A GB1792667 A GB 1792667A GB 1792667 A GB1792667 A GB 1792667A GB 1174165 A GB1174165 A GB 1174165A
Authority
GB
United Kingdom
Prior art keywords
radical
group
general formula
carbon atoms
hydrogen atom
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
GB1792667A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1174165A publication Critical patent/GB1174165A/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
    • C07D239/42—One nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,174,165. Pyrimidine derivatives. BADISCHE ANILIN - & SODA - FABRIK A.G. 19 April, 1967 [20 April, 1966 (3)], No. 17926/67. Heading C2C. 5-Halo-pyrimidine derivatives having the general formula wherein R<SP>1</SP> is a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl radical or an aryl radical bearing one or more substituents which are inert under the reaction conditions; X is a halogen atom; and Y is (a) a -NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, an alkyl, cycloalkyl or aralkyl radical or an aryl radical optionally substituted by one or more substituents which are inert under the reaction conditions or together form an alkylene radical having 2 to 6 carbon atoms in which one methylene group may be replaced by an oxygen or sulphur atom or by an or (in which R<SP>5</SP> is an alkyl, cycloalkyl or phenyl radical) group; or (b) a -NR<SP>2</SP>NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>2</SP> is a hydrogen atom or a methyl group and R<SP>3</SP> and R<SP>4</SP> are as defined above, are prepared by reaction of a 4,5-dihalopyrimidine of the general formula with a compound of the Formula HY or an alkali metal or alkaline earth metal salt thereof, at 30-200‹ C. Pyrimidine derivatives of the first general formula above wherein R<SP>1</SP> is an aryl radical having 6 to 12 carbon atoms; X is a chlorine or bromine atom; and Y is (a) a -NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms, an aralkyl radical having 7 to 9 carbon atoms or an aryl group, or together form an alkylene radical having 2 to 6 carbon atoms in which one methylene group may be replaced by an oxygen atom; or (b) a-NR<SP>2</SP>- NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>2</SP> is a hydrogen atom or a methyl group and R<SP>3</SP> and R<SP>4</SP> are as defined above in this paragraph, are novel compounds. 4,5 - Dihalopyrimidines of the second general formula above are prepared by reaction of (i) an acrylic acid derivative of the general formula wherein R<SP>6</SP> is a halogen atom or an alkoxy group, R<SP>7</SP> is an alkoxy group or a -NR<SP>8</SP>R<SP>9</SP> group in which R<SP>8</SP> and R<SP>9</SP> are each a hydrogen atom or a C 1-4 alkyl group; or (ii) a propionic acid derivative of the general formula wherein R<SP>7</SP> and X are as defined above and R<SP>10</SP> and R<SP>11</SP> are alkyl groups, with an amidine of the general formula or an acid addition salt thereof from which the amidine can be liberated by reaction with a base, at 30-120‹ C. in the presence of a base; and reaction of the resulting 5-halo-4-hydroxypyrimidine of the general formula with phosgene, oxalyl chloride, a chloride, bromide or iodide of trivalent or pentavalent phosphorus, or an oxychloride or oxybromide of pentavalent phosphorus or of tetravalent or hexavalent sulphur at 30-200‹ C.
GB1792667A 1966-04-20 1967-04-19 Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position Expired GB1174165A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEB0086748 1966-04-20
DEB0086749 1966-04-20
DEB0086751 1966-04-20

Publications (1)

Publication Number Publication Date
GB1174165A true GB1174165A (en) 1969-12-17

Family

ID=27209348

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1792667A Expired GB1174165A (en) 1966-04-20 1967-04-19 Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position

Country Status (1)

Country Link
GB (1) GB1174165A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2158081A1 (en) * 1971-10-28 1973-06-15 Delalande Sa

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2158081A1 (en) * 1971-10-28 1973-06-15 Delalande Sa

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees