Sodium Bicarbonate → 2-(Methylsulfonyl)-4-(pyridin-3-yl)pyrimidine

HRID 1514437Notes

Reaction equation

HRID 1514437 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.O[O:16][S:17]([O-:19])=O.[K+].[C:21]([O-])(O)=O.[Na+]>CO>[CH3:21][S:17]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1)(=[O:19])=[O:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 28242882-(Methylthio)-4-(pyridin-3-yl)pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 469098552-(Methylsulfonyl)-4-(pyridin-3-yl)pyrimidineYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methylsulfanyl-4-pyridin-3-yl-pyrimidine (1.18 g, 5.81 mmol) in MeOH (45 ml) was cooled at 0° C., then an aqueous solution of oxone (10.7 g, 17.45 mmol in 45 ml of water) was slowly added. After stirring 1.5 hours at room temperature, the mixture was basified with 5% NaHCO3 and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 846 mg of the title compound that was used in the next step without further purification (61% yield).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-29b4b7eae467424b97ad417dbe91c1cd
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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