Sodium Hydroxide → 5-Bromo-2-(methylsulphonyl)pyrimidine

HRID 38220Notes

Reaction equation

HRID 38220 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[OH:10]OS([O-])=O.[K+].[OH-:16].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:8]([CH3:9])(=[O:10])=[O:16])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 47385645-Bromo-2-(methylsulfanyl)pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 3192865-Bromo-2-(methylsulphonyl)pyrimidineYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-2-methylsulfanylpyrimidine (10.0 g, 48.8 mmol) in methanol (195 mL) were added a solution of Oxone® (94.6 g, 154 mmol, 3.16 eq) in water (500 mL and aq. 4 N sodium hydroxide (40 mL, 160 mmol, 3.28 eq.) portionwise and in an alternating addition mode to maintain pH between 2 and 3 at a temperature of 0° C. After complete addition, the mixture was allowed to stir for 2 h at room temperature. Water (500 mL) was added, and the mixture was extracted with ethyl acetate (2×500 mL). The aqueous layer was adjusted to pH 7 by addition of aq. sodium hydroxide, and was again extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated to give 9.23 g (80% yield) of the desired sulfone which was used without further purification.

Workup

  1. additionin an alternating addition mode
  2. additionAfter complete addition
  3. extractionthe mixture was extracted with ethyl acetate (2×500 mL)
  4. additionThe aqueous layer was adjusted to pH 7 by addition of aq. sodium hydroxide
  5. extractionwas again extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-596e1db344f24d2bbd79e0471a631c11
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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