Dimethyl Sulfoxide → 5-bromo-1-methylpyrimidin-2(1H)-one

HRID 1693080Notes

Reaction equation

HRID 1693080 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.CS(C)=O.Br.[Br:14][C:15]1[CH:16]=[N:17][C:18](O)=[N:19][CH:20]=1>O>[Br:14][C:15]1[CH:20]=[N:19][C:1](=[O:4])[N:17]([CH3:18])[CH:16]=1

Participants

6

Conditions

Temperature
15 °C

Procedure

With cooling with ice, potassium carbonate (7.56 g, 54.7 mmol) and methyl iodide (1.27 ml, 20.3 mmol) were added to a dimethyl sulfoxide (100 mL) solution of 5-bromo-2-hydroxypyrimidine hydrobromide (4.0 g, 15.6 mmol), and stirred at 15° C. for 16 hours. Water was added to the reaction mixture, and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was suspended in ethyl acetate, then filtered and dried to obtain the entitled compound (1.33 g, 45%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-99706d6531d642b28ffdd1054711be53
Source dataset
uspto-grants-2012_04
Patent number
US08158652B2

Reaction notes

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