Acetic Acid → 3-(4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660745
C(O)(=O)C.[Br:5]N1C(=O)CCC1=O.[CH2:13]([CH:15]([C:18]1[N:23]2[N:24]=[C:25]([CH3:38])[C:26]([C:27]3[S:31][C:30]([C:32]4[N:33]([CH3:37])[N:34]=[CH:35][N:36]=4)=[N:29][CH:28]=3)=[C:22]2[N:21]=[C:20]([CH3:39])[CH:19]=1)[CH2:16][CH3:17])[CH3:14]>C(#N)C>[Br:5][C:28]1[N:29]=[C:30]([C:32]2[N:33]([CH3:37])[N:34]=[CH:35][N:36]=2)[S:31][C:27]=1[C:26]1[C:25]([CH3:38])=[N:24][N:23]2[C:18]([CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])=[CH:19][C:20]([CH3:39])=[N:21][C:22]=12

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 674282857-(1-ethyl-propyl)-2,5-dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 248989763-(4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

Add acetic acid (1 mL) and N-bromosuccinimide (4.1 g, 22 mmol) to a solution of 7-(1-ethyl-propyl)-2,5-dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-pyrazolo[1,5-a]pyrimidine (8 g, 21 mmol) in acetonitrile (80 mL). Stir the mixture 2 h at 22° C. Then evaporate the solvent and add water (50 mL) and methyl-t-butyl ether (100 mL) to the resulting residue. Separate the organic portion, dry over sodium sulfate, filter, and evaporate the solvent. Recrystallize the resulting residue from isopropyl alcohol to afford the title compound (8.7 g, 90%). ES/MS (m/z): (79Br/81Br) 460/462 (M+1)+.

Aufarbeitung

  1. customThen evaporate the solvent
  2. additionadd water (50 mL) and methyl-t-butyl ether (100 mL) to the resulting residue
  3. customSeparate the organic portion
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. customevaporate the solvent
  7. customRecrystallize the resulting residue from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-be3f95debbfb4ed4adc04edddfd1230f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030304B2

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