Pyrazole → 2-Amino-4-methylsulfanyl-6-pyrazol-1-yl-pyrimidine-5-carbonitrile

HRID 1356091

반응식

HRID 1356091 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[K+].[NH2:8][C:9]1[N:14]=[C:13](Br)[C:12]([C:16]#[N:17])=[C:11]([S:18][CH3:19])[N:10]=1>COCCOCCOC>[NH2:8][C:9]1[N:10]=[C:11]([S:18][CH3:19])[C:12]([C:16]#[N:17])=[C:13]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[N:14]=1

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 82127Potassium hydrideHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

생성물 1

HCID 185075242-Amino-4-methylsulfanyl-6-pyrazol-1-yl-pyrimidine-5-carbonitrile수율 27.4%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 500 mg (7.34 mmol) pyrazole in 15 ml diglyme at room temperature under argon was added 0.90 ml (7.34 mmol) potassium hydride (35% dispersion in oil) and the reaction mixture heated at 60° C. for 2 hours. 1.50 g (6.12 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile was then added and the reaction mixture heated at 60° C. for 16 h, then cooled to room temperature, 2 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/3) afforded 390 mg (27%) 2-amino-4-methylsulfanyl-6-pyrazol-1-yl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 232 (M+, 61), 231 ([M—H]+, 100).

후처리

  1. temperaturethe reaction mixture heated at 60° C. for 16 h
  2. temperaturecooled to room temperature
  3. addition2 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo

출처 및 근거

ORD 기록
ord-566ca670243e4903a470ff475487d0f6
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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