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

HRID 1356091

Reaktionsgleichung

Reaktionsgleichung von HRID 1356091
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 185075242-Amino-4-methylsulfanyl-6-pyrazol-1-yl-pyrimidine-5-carbonitrileAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-566ca670243e4903a470ff475487d0f6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

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