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

HRID 1046103

Reaction equation

HRID 1046103 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 584852862-(5-Bromopyrimidin-2-yl)propan-2-olYield 46.77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-6601085bd313461aa1c2e3612db19e05
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Linked notes

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