Ammonium Chloride → 7-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660751
C([Li])CCC.[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:25])[C:19]([C:20]3[S:24][CH:23]=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:26])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[CH3:27][O:28][CH2:29]I.[Cl-].[NH4+]>C1COCC1>[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:25])[C:19]([C:20]3[S:24][C:23]([CH2:27][O:28][CH3:29])=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:26])[CH:12]=1)[CH2:9][CH3:10])[CH3:7]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 139376Iodomethyl methyl etherHCID 674299217-(1-Ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 674280047-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, add n-butyl lithium (2.5 M in hexane, 0.4 mL, 1.0 mmol) to a solution of 7-(1-ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine (300 mg, 1.0 mmol) in THF (3 mL) at −78° C. Stir 30 min and add 1-iodomethyl methyl ether (205 mg, 1.2 mmol). Continue stirring for one hour and then slowly warm up to room temperature and stir overnight. Quench the reaction by adding saturated ammonium chloride solution and extract with ethyl acetate. Wash the organic layer with brine, dry over sodium sulfate, filter, and concentrate under vacuum to a residue. Purify the crude material by flash chromatography, eluting with hexanes/ethyl acetate (10/2) to give the title compound as a yellow foam (184 mg). MS (APCI) m/z 345.3 (M+1)+.

Aufarbeitung

  1. stirringContinue stirring for one hour
  2. stirringstir overnight
  3. customQuench
  4. customthe reaction
  5. extractionextract with ethyl acetate
  6. washWash the organic layer with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum to a residue
  10. customPurify the crude material by flash chromatography
  11. washeluting with hexanes/ethyl acetate (10/2)

Quellen und Nachweise

ORD-Eintrag
ord-f6926211565b4335b21e8343b767da51
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030304B2

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