Water → (S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

HRID 539030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539030
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:15][C@H:14]([CH:16]([CH3:18])[CH3:17])[N:13]([C:19]2[CH:24]=[CH:23][N:22]3[N:25]=[CH:26][C:27]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[N:38]=[CH:37][N:36]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:35]=5)=[CH:30][CH:29]=4)=[C:21]3[N:20]=2)[C:12]1=[O:47])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:8][CH2:9][CH2:10][N:11]1[CH2:15][C@H:14]([CH:16]([CH3:18])[CH3:17])[N:13]([C:19]2[CH:24]=[CH:23][N:22]3[N:25]=[CH:26][C:27]([C:28]4[CH:29]=[CH:30][C:31]([C:34]5[N:38]=[CH:37][N:36]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:45])([CH3:44])[CH3:46])[N:35]=5)=[CH:32][CH:33]=4)=[C:21]3[N:20]=2)[C:12]1=[O:47]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67034472(S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

Produkt 1

HCID 67034260(S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.18 g, 0.27 mmol) in THF was added Tetra-n-butylammonium fluoride (1 mmol, 1 mL, 1M solution in THF) and the reaction was stirred at ambient temperature for 3 hours. The reaction was poured into water and extracted into EtOAc. The combined organic layers were washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The crude material was chromatographed using 3% MeOH/dichloromethane as eluent to yield (S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.15 g, 100%).

Aufarbeitung

  1. extractionextracted into EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-4d13530349004d6a97afaaa41ae037f2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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