Dimethylformamide → 5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624691
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.O=P(Cl)(Cl)Cl.CN([CH:23]=[O:24])C>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:23]=[O:24])=[C:4]2[N:3]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 581966065-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine

Produkt 1

HCID 581966475-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Versuchsvorschrift

To 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (156 mg, 0.75 mmol) in DMF was added POCl3 (205 μl, 2.25 mmol). The mixture was stirred at room temperature for 3 hours. Ice was added to quench excess POCl3 then the mixture was neutralized with 1M NaOH. DCM was added and the product was extracted three times. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. Some residual DMF could not be removed. LCMS (M+1=237)

Aufarbeitung

  1. additionIce was added
  2. customto quench excess POCl3
  3. additionDCM was added
  4. extractionthe product was extracted three times
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7105e654123441e9aef2589b08cb054b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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