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Water → 2-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol

HRID 82146
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 82146
[BH4-].[Li+].[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[C:14](OC)=[O:15])[CH:5]=1.O>C(O)C>[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[CH2:14][OH:15])[CH:5]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 70817219HCID 70817219, Verbindung

Produkt 1

HCID 708175262-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Lithium borohydride (32.3 mL, 64.6 mmol, 2.0 M in THF) was added to methyl 2-(5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate (8.92 g, 25.9 mmol) (see Preparation 21) in ethanol (70 mL). The mixture was stirred at room temperature for 17 hours then water (70 mL) was added. The mixture was evaporated in vacuo then the residue was partitioned between DCM (250 mL) and water (50 mL). The aqueous phase was extracted with DCM:MeOH (90:10, 2×250 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford the title compound as an off-white solid in 100% yield, 8.20 g.

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between DCM (250 mL) and water (50 mL)
  3. extractionThe aqueous phase was extracted with DCM:MeOH (90:10, 2×250 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-74a5983e4f464f568c56ec53293c3908
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846698B2

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