(E)-2,3-dibromo-4-oxobut-2-enoic acid → 5-Bromo-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid

HRID 1915899ノート

反応式

HRID 1915899 の反応式
[O-]CC.[Na+].[F:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[NH:9].Br/[C:16](=[C:20](/[Br:23])\[CH:21]=O)/[C:17]([OH:19])=[O:18]>C(O)C>[Br:23][C:20]1[C:16]([C:17]([OH:19])=[O:18])=[N:9][C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[F:5])=[N:10][CH:21]=1

参加物

5

反応物 3

HCID 2723705(E)-2,3-dibromo-4-oxobut-2-enoic acidHCID 2723922Sodium ethoxideHCID 43230592-Fluorobenzamidine

生成物 1

HCID 821686735-Bromo-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Sodium ethoxide (21 mass % in ethanol; 8.69 mL, 23.268 mmol) was added to an ice-bath cooled mixture of 2-fluorobenzamidine (2.71 g, 15.512 mmol) in ethanol (100 mL). The resulting mixture was allowed to warm to room temperature and stirred at rt (room temperature) under nitrogen for 30 min. To the reaction mixture was added a solution of (E)-2,3-dibromo-4-oxo-but-2-enoic acid (2.00 g, 7.7561 mmol) in ethanol (20 ml). The mixture was heated at 50° C. for 3 h. After cooling to RT, the reaction was concentrated in vacuo. Water and 1M NaOH (˜50 ml) were added and the aqueous mixture was extracted with EtOAc. The aqueous phase was acidified to pH4 with 1N HCl (about 30 ml), then extracted with EtOAc 3×. Combined organic extracts were dried over sodium sulfate, filtered and concentrated to gave 5-bromo-2-(2-fluorophenyl)pyrimidine-4-carboxylic acid, 770 mg.

後処理

  1. temperaturecooled
  2. temperatureThe mixture was heated at 50° C. for 3 h
  3. temperatureAfter cooling to RT
  4. concentrationthe reaction was concentrated in vacuo
  5. additionWater and 1M NaOH (˜50 ml) were added
  6. extractionthe aqueous mixture was extracted with EtOAc
  7. extractionextracted with EtOAc 3×
  8. dry with materialCombined organic extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f66b542cb56249499a1599913708a013
出典データセット
uspto-grants-2013_12
特許番号
US08614206B2

反応ノート

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