5-Bromo-2,4-dichloropyrimidine → 5-Bromo-2-chloro-4-methoxypyrimidine

HRID 1623022Notes

Reaction equation

HRID 1623022 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][O-:11].[Na+]>CO>[Br:1][C:2]1[C:3]([O:11][CH3:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 36631435-Bromo-2-chloro-4-methoxypyrimidineYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-bromo-2,4-dichloropyrimidine (500 mg, 2.19 mmol) in MeOH (5 mL) was added a 30% solution of sodium methoxide (0.40 mL, 2.26 mmol). The reaction mixture was stirred at RT for 2 h then concentrated. The residue was dissolved in water (5 mL) and extracted with EA (3×5 mL). The combined organic layer was washed with brine, dried over MgSO4 and concentrated to afford 432 mg (88%) of 5-bromo-2-chloro-4-methoxypyrimidine as white solid. LCMS-ESI (m/z) calculated for C5H4BrClN2O: 223.4; found 224.2 [M+H]+, tR=7.66 min. (Method 2).

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. extractionextracted with EA (3×5 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa2be3941d1a4efbb60f4bdcaac9cb84
Source dataset
uspto-grants-2014_07
Patent number
US08778923B2

Reaction notes

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