Sodium hydride → HCID 58056314, 화합물

HRID 1773567

반응식

HRID 1773567 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 58056314HCID 58056314, 화합물수율 21.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-822402bd765b44ba96d520e40ab69b06
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255110B2

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