Tetrabutylammonium Fluoride → (2-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)thiazol-5-yl)methanol

HRID 1684952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684952
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[S:13][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:15][N:16]=2)=[N:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[S:13][C:14]([CH2:17][OH:18])=[CH:15][N:16]=2)=[N:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 57541342N-(5-bromoimidazo[1,2-a]pyrazin-8-yl)-5-((tert-butyldimethylsilyloxy)methyl)thiazol-2-amine

Produkt 1

HCID 57541339(2-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)thiazol-5-yl)methanolAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of Step 1 (0.125 g, 0.28 mmol) is dissolved in THF (2 mL). To this solution is added TBAF solution (1M in THF, 0.31 mL, 0.31 mmol) and the reaction is stirred at room temperature overnight. The reaction is condensed and the residue purified by gradient column chromatography eluting with dichloromethane—5% methanolic ammonia (7 N) in dichloromethane to give the alcohol (64 mg, 69%). LCMS: Rt 2.54 min (97.7%). MS (MH+, m/z) 326.

Aufarbeitung

  1. customcondensed
  2. customthe residue purified by gradient column chromatography
  3. washeluting with dichloromethane—5% methanolic ammonia (7 N) in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-eae303cf81374bae9d7aebd7efdc5a5a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148369B2

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