Acetic Acid → 6-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 418284

反応式

HRID 418284 の反応式
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].C(O)(=O)C.[Br:18][CH:19]([CH:22]=O)[CH:20]=O>C(O)C>[Br:18][C:19]1[CH:20]=[N:1][C:2]2[N:6]([N:5]=[CH:4][C:3]=2[C:7]([OH:9])=[O:8])[CH:22]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2 回HCID 749452-BromopropanedialHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylate

生成物 1

HCID 252207936-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid収率 50.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
70 °C

実験手順

A solution of ethyl 5-amino-1H-pyrazole-4-carboxylate (2 g, 12.89 mmol) and sodium hydroxide (19.34 mL, 38.7 mmol) (aqueous, 2M) in ethanol (30 mL) was heated at 80° C. overnight. The reaction mixture was concentrated in vacuo to give a crude mixture of carboxylate and sodium hydroxide. The crude mixture was dissolved in ethanol (4 mL) and acetic acid (14 mL, 245 mmol). Whilst stirring the mixture, bromomalonaldehyde (1.947 g, 12.90 mmol) was added and then the mixture heated to 70° C. for 1 h. The reaction mixture was allowed to cool and the precipitate was filtered and washed with ethanol. The solid product was dried in a vacuum oven to give the title compound (1.589 g).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a crude
  3. additionwas added
  4. temperatureto cool
  5. filtrationthe precipitate was filtered
  6. washwashed with ethanol
  7. customThe solid product was dried in a vacuum oven

出典と根拠

ORDレコード
ord-5249bd5d12a84c86b40b10be0ee46e27
出典データセット
uspto-grants-2012_01
特許番号
US08093249B2

関連ノート

読み込み中…