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Dimethylformamide → 4-Methyl-4-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

HRID 1962690
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1962690
CS(O[CH2:6][CH2:7][C:8]([CH3:24])([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)[CH3:9])(=O)=O.[CH3:25][N:26](C=O)C.[C-]#N.[Na+]>O>[CH3:9][C:8]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)([CH3:24])[CH2:7][CH2:6][C:25]#[N:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 57477613HCID 57477613, Verbindung

Produkt 1

HCID 177548084-Methyl-4-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrileAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

3-methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate (2.97 g, 8.50 mmol), DMF (120 mL) and sodium cyanide (6.21 g, 0.127 mol) were distributed evenly into six 20 mL microwavable vessels, each of which was heated in the microwave reactor for 4000 seconds at 125° C. The contents of the vials were combined and were diluted with 400 mL water and extracted with five 150 mL portions of ethyl acetate. The combined extracts were dried over sodium sulfate, and the solvent was removed in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.40 g, 59%).

Aufarbeitung

  1. extractionextracted with five 150 mL portions of ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe crude residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c25620ed7d5246e4822dec07642eb792
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415362B2

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