Lithium Hydroxide → 7-Hydroxy-5-phenylpyrazolo[1,5-c]pyrimidine-3-carboxylic acid

HRID 386649ノート

反応式

HRID 386649 の反応式
O[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([O:13]CC)=[O:12])=[C:6]2[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]=1.[OH-:22].[Li+]>CO>[OH:22][C:6]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:2]2[CH:3]=[C:4]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:5]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 178469958HCID 178469958、化合物

生成物 1

HCID 1785248137-Hydroxy-5-phenylpyrazolo[1,5-c]pyrimidine-3-carboxylic acid収率 79%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

Ethyl 7-hydroxy-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate (3.1 g, 11 mmol) was taken into 27 mL methanol and 2 M aqueous lithium hydroxide (27 mL) and heated in an 80° C. oil bath for 4 h. The solution was allowed to cool to room temperature and concentrated in vacuo to remove methanol. The subsequent basic aqueous mixture was washed with ethyl acetate (10% methanol) and then acidified to pH 3 using concentrated hydrochloric acid. A solid formed and was collected via vacuum filtration to yield 2.2 g (79%) of crystalline 7-hydroxy-5-phenylpyrazolo[1,5-c]pyrimidine-3-carboxylic acid. 1H NMR (400 MHz, d6-DMSO): 8.21 (s, 1H), 7.76 (m, 2H), 7.57 (m, 3H), 6.24 (s, 1H).

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove methanol
  4. washThe subsequent basic aqueous mixture was washed with ethyl acetate (10% methanol)
  5. customA solid formed
  6. filtrationwas collected via vacuum filtration

出典と根拠

ORDレコード
ord-3cd989cc370e4e6fb40eb4759acc3ff4
出典データセット
uspto-grants-2013_02
特許番号
US08372851B2

反応ノート

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