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

HRID 1660740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660740
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([CH:11]([C:14]1[N:19]2[N:20]=[C:21]([CH3:28])[C:22]([C:23]3[S:27][CH:26]=[N:25][CH:24]=3)=[C:18]2[N:17]=[C:16]([CH3:29])[CH:15]=1)[CH2:12][CH3:13])[CH3:10].[I:30]N1C(=O)CCC1=O.[Cl-].[NH4+]>C1COCC1>[CH2:9]([CH:11]([C:14]1[N:19]2[N:20]=[C:21]([CH3:28])[C:22]([C:23]3[S:27][C:26]([I:30])=[N:25][CH:24]=3)=[C:18]2[N:17]=[C:16]([CH3:29])[CH:15]=1)[CH2:12][CH3:13])[CH3:10]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 120273N-IodosuccinimideHCID 2724682Lithium diisopropylamideHCID 674299217-(1-Ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 674287187-(1-Ethyl-propyl)-3-(2-iodo-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Add a freshly prepared solution of lithium di-i-propylamide (150 ml; 62 4 mmol, 0.6 M in THF) to a mixture of 7-(1-ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine, (17.8 g, 62 4 mmol) in THF (100 mL) at −78° C. under a nitrogen atmosphere, keeping the temperature below −74° C. during the addition. Stir the mixture at −78° C. for one hour and then add a solution of N-iodosuccinimide (15 g, 63 mmol) in THF (100 mL) keeping temperature below −74° C. Warm the reaction gradually to 22° C. and then add a 10% aqueous solution of ammonium chloride (300 mL). Separate the organic layer and wash the aqueous layer with methyl-t-butyl ether (2×200 mL). Combine the organic layers, dry over sodium sulfate, filter, and evaporate the solvent. Purify the resulting residue by silica gel chromatography, eluting with hexanes/acetone (5/1) to afford the title compound (15 g, 60%). ES/MS m/z 427 (M+1)+.

Aufarbeitung

  1. customthe temperature below −74° C.
  2. additionduring the addition
  3. customtemperature below −74° C
  4. temperatureWarm
  5. customthe reaction gradually to 22° C.
  6. customSeparate the organic layer
  7. washwash the aqueous layer with methyl-t-butyl ether (2×200 mL)
  8. dry with materialCombine the organic layers, dry over sodium sulfate
  9. filtrationfilter
  10. customevaporate the solvent
  11. customPurify the resulting residue by silica gel chromatography
  12. washeluting with hexanes/acetone (5/1)

Quellen und Nachweise

ORD-Eintrag
ord-6be71557092b4cb98078b6743b1f64b5
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030304B2

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