Hydroxylamine → 4-Methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-amine

HRID 241435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241435
[CH3:1][C:2]1[N:3]=[C:4]2[N:9]=CC=C[N:5]2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.NO>CCO>[CH3:1][C:2]1[N:3]=[C:4]([NH2:9])[NH:5][C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

Produkt 1

HCID 1784333994-Methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-amineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Stir a mixture of 2-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine (180 g, 649.2 mmol, 1 equiv) in EtOH (1.4 L) and hydroxylamine (159 ml, 2.596 mol, 4 equiv) at an internal temperature of 82° C. for 48 hours. Cool the mixture, and concentrate to dryness. Dilute the residue with DCM (1.5 L), and wash sequentially with water (2×500 ml) and brine (500 ml). Dry the organic phase over MgSO4; filter; collect the filtrate and; and remove the solvent in vacuo to give a yellow gum. Purify the resulting material by flash chromatography on silica gel (2 kg), eluting with a gradient of 4:1:0.02 DCM/MeOH/NH3 to obtain the title compound as a yellow foam (95% yield). MS (m/z) 242 (M+1).

Aufarbeitung

  1. temperatureCool the mixture
  2. concentrationconcentrate to dryness
  3. additionDilute the residue with DCM (1.5 L)
  4. washwash sequentially with water (2×500 ml) and brine (500 ml)
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. customcollect the filtrate
  8. customand remove the solvent in vacuo
  9. customto give a yellow gum
  10. customPurify the resulting material by flash chromatography on silica gel (2 kg)
  11. washeluting with a gradient of 4:1:0.02 DCM/MeOH/NH3

Quellen und Nachweise

ORD-Eintrag
ord-9ed8440d7c3c47dc8cf5013c054f3279
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648200B2

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