Hydrochloric Acid → 3-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 277437

反応式

HRID 277437 の反応式
N(OC(C)(C)C)=[O:2].N[C:9]1[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[CH:12]=[C:11]([F:18])[C:10]=1[N:19]1[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]1=[O:31].Cl>S([O-])([O-])(=O)=O.[Cu+2].[Cu-]=O.O.[N+]([O-])([O-])=O.[Cu+2].O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(#N)C>[Cl:17][C:13]1[CH:12]=[C:11]([F:18])[C:10]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[C:9]([OH:2])[C:14]=1[O:15][CH3:16]

参加物

8

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 183145373-(2-Amino-4-chloro-6fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione

生成物 1

HCID 572512883-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

試薬・触媒・溶媒 4

HCID 24462Copper Sulfate触媒HCID 167780Copper(II) nitrate hemipentahydrate触媒HCID 178419072HCID 178419072、化合物触媒HCID 6342Acetonitrile溶媒2 回

実験手順

An acetonitrile (10 ml) solution of copper (II) sulfate (0.52 g, 3.26 mmol), copper (I) oxide (0.47 g, 3.26 mmol) and copper (II) nitrate hemipentahydrate (0.76 g, 3.26 mmol) was stirred at −30° C., and added with tert-butyl nitrite (0.41 g, 3.97 mmol) and then an acetonitrile (3 ml) solution of 3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.94 g, 2.56 mmol). After stirred for 16 hr (−30° C. to room temperature), the mixture was poured into cold 5% hydrochloric acid (30 ml) and then extracted with ethyl acetate (20 ml×3). The organic phase was washed with brine and dried over Na2SO4. Preparative TLC was used for purification (silica gel plates, 2000 microns, ether). Yield: 0.16 g, 0.44 mmol.

後処理

  1. extractionextracted with ethyl acetate (20 ml×3)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customPreparative TLC was used for purification (silica gel plates, 2000 microns, ether)

出典と根拠

ORDレコード
ord-1957e37683444cdcbe5a1cf20c9e049f
出典データセット
uspto-grants-2002_03
特許番号
US06355799B1

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