Sodium hydride → HCID 58056314、化合物

HRID 1773567

反応式

HRID 1773567 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][NH:11][C:12]=1[NH2:13])=[O:7])[CH3:4].[O:14]1[CH2:19][CH2:18][CH2:17][C:16]([CH:20]=O)=[CH:15]1>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:20]=[C:16]([CH2:17][CH2:18][CH2:19][OH:14])[CH:15]=[N:13][C:12]=12)=[O:7])[CH3:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylateHCID 27361513,4-dihydro-2H-pyran-5-carbaldehyde

生成物 1

HCID 58056314HCID 58056314、化合物収率 21.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% suspension in mineral oil, 350 mg, 8.78 mmol) was added, at 0° C., to a solution of 5-amino-1H-pyrazole-4-carboxylic acid ethyl ester (1.4 g, 8.9 mmol) and 5,6-dihydro-4H-pyran-3-carbaldehyde (0.5 g, 4.5 mmol) in anhydrous N,N-dimethylformamide (10 mL) and the resulting mixture was stirred, at 0° C., for 30 minutes. The reaction mixture was stirred at room temperature overnight and then heated at 50° C. for 2 hours. The resulting mixture was partitioned between water and ethyl acetate and the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography to afford 0.24 g of 6-(3-hydroxy-propyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester as a white solid. MS=250 [M+H]+.

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. temperatureheated at 50° C. for 2 hours
  3. customThe resulting mixture was partitioned between water and ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-822402bd765b44ba96d520e40ab69b06
出典データセット
uspto-grants-2016_02
特許番号
US09255110B2

関連ノート

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