N,N-Dimethylaniline → 7-Chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 624817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624817
P(Cl)(Cl)([Cl:3])=O.CN(C)C1C=CC=CC=1.O[C:16]1[N:21]2[N:22]=[CH:23][CH:24]=[C:20]2[N:19]=[C:18]([S:25][CH3:26])[C:17]=1[C:27]#[N:28]>>[Cl:3][C:16]1[N:21]2[N:22]=[CH:23][CH:24]=[C:20]2[N:19]=[C:18]([S:25][CH3:26])[C:17]=1[C:27]#[N:28]

Komponenten

4

Edukt 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178503357HCID 178503357, Verbindung

Produkt 1

HCID 220480807-Chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrileAusbeute 80 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Under nitrogen gas atmosphere, phosphorous oxychloride (9.4 mL, 101.3 mmol) and dimethylaniline (2.6 mL, 20.3 mmol) was added successively to the intermediate, 7-hydroxy-5-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile, prepared above (4.1 g, 19.7 mmol). The mixture was heated at 110° C. for 4 hours then excess POCl3 was removed under vacuum. The residue was made basic with 3N NaOH solution (pH=9-10) and extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The residue was purified by recrystallization from ethyl acetate hexanes to provide the product, 7-chloro-5-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile (80% yield). LCMS (M+1=225)

Aufarbeitung

  1. customprepared above (4.1 g, 19.7 mmol)
  2. customexcess POCl3 was removed under vacuum
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by recrystallization from ethyl acetate hexanes

Quellen und Nachweise

ORD-Eintrag
ord-008a7042325a4d97a9a0a3ac330f4368
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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