Phosphorus oxychloride → 4-chloro-1-(2,3-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1098234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098234
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[N:14]1[C:18]2=[N:19][CH:20]=[N:21][C:22](O)=[C:17]2[CH:16]=[N:15]1>>[Cl:3][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:14]([C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=3[Cl:6])[N:15]=[CH:16][C:17]=12

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178517919HCID 178517919, Verbindung

Produkt 1

HCID 574386164-chloro-1-(2,3-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidineAusbeute 57,5 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phosphorus oxychloride (26.5 ml, 284.60 mmol) was added to 1-(2,3-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate AR3) (4 g, 14.23 mmol), at ambient temperature. The resulting mixture was stirred at 100° C. for 4 hours. Allowed to cool to Ambient temperature. The reaction mixture was evaporated to near dryness, dissolved in toluene, evaporated, re-dissolved in toluene and evaporated to dryness again. The solid was triturated with EtOH. A solid was filtered off and dried under vacuum to give the product (2.450 g, 57.5%). 1H NMR (400 MHz, DMSO) δ 7.65 (1H, m), 7.73-7.75 (1H, dd), 7.94-7.97 (1H, dd), 8.83 (1H, s), 8.91 (1H, s); m/z (ES+) (M+H)+=518; HPLC tR=1.89 min.

Aufarbeitung

  1. temperatureAllowed to cool to Ambient temperature
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in toluene
  4. customevaporated
  5. dissolutionre-dissolved in toluene
  6. customevaporated to dryness again
  7. customThe solid was triturated with EtOH
  8. filtrationA solid was filtered off
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c3802c4ea5754c18a853ffdd4124bb8b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143263B2

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