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

HRID 589170Notes

Reaction equation

HRID 589170 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 178418573HCID 178418573, compound

Product 1

HCID 584852862-(5-Bromopyrimidin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(5-bromopyrimidin-2-yl)ethanone (100 mg, 0.5 mmol) in THF (10 mL) at −78° C. was added methylmagnesium bromide (1.4M solution, 3.6 mL, 5 mmol). The reaction mixture was stirred for an additional 20 minutes until LC/MS analysis indicated that the reaction was complete. Quenching with saturated NH4Cl, extraction with EtOAc and drying over MgSO4, afforded the crude residue which was taken forward as is in the next step.

Workup

  1. customQuenching with saturated NH4Cl, extraction with EtOAc
  2. dry with materialdrying over MgSO4

Sources & evidence

ORD record
ord-ef0297078d904383861d5ebed6d1655c
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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