1-(5-Bromopyrimidin-2-yl)ethan-1-one → 2-(5-Bromopyrimidin-2-yl)propan-2-ol

HRID 1046103

Reaktionsgleichung

Reaktionsgleichung von HRID 1046103
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[CH3:11][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])([CH3:11])[CH3:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-oneHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 584852862-(5-Bromopyrimidin-2-yl)propan-2-olAusbeute 46,77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-(5-bromopyrimidin-2-yl)ethanone (99 mg, 0.50 mmol) in THF (10 mL) was added MeMgBr (1.65 mL, 4.95 mmol) at −78° C. under nitrogen. The formed solution was stirred at −78° C. for 20 min, quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give an oil, which was purified by prep TLC (3:1 PE/EtOAc) to give 2-(5-bromopyrimidin-2-yl)propan-2-ol (50 mg, yield: 46.77%).

Aufarbeitung

  1. customquenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by prep TLC (3:1 PE/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6601085bd313461aa1c2e3612db19e05
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569292B2

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