Hydrochloric Acid → 7-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine

HRID 2036952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036952
[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11](Cl)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].Cl.O1CCOCC1>C(O)C>[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([Cl:19])[CH:21]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 312751,4-DioxaneHCID 583137227-(Benzylthio)-5-chloropyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 583150077-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To the reaction flask, 7-(benzylthio)-5-chloropyrazolo[1,5-a]pyrimidine (3.45 g, 12.5 mmol) was added along with 3-chloroaniline (3.3 mL, 31.3 mmol), 4N HCl in dioxane (3.1 mL, 12.5 mmol), and ethanol (42 mL). The reaction was stirred at reflux for 12 hours then cool to room temperature. Excess solvent was removed under vacuum and the residue was diluted with water. The mixture was made basic with 3N NaOH, filtered and washed with water. The product, 7-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine, was collected as a solid in 90% yield after drying under vacuum overnight. LCMS (M+1=376)

Aufarbeitung

  1. temperatureat reflux for 12 hours
  2. customExcess solvent was removed under vacuum
  3. additionthe residue was diluted with water
  4. filtrationfiltered
  5. washwashed with water
  6. customThe product, 7-(benzylthio)-N-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine, was collected as a solid in 90% yield
  7. customafter drying under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-ab1a63816ac441e2bef7e9ac3e4c35a0
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

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