Methanol → 2-Methanesulfonyl-5-methyl-4-pyridin-3-yl-pyrimidine

HRID 1514408Notes

Reaction equation

HRID 1514408 reaction equation
[CH3:1][C:2]1[C:3]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:4][C:5](SC)=[N:6][CH:7]=1.O[O:17][S:18]([O-:20])=O.[K+].[CH3:22]O>>[CH3:22][S:18]([C:5]1[N:4]=[C:3]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:2]([CH3:1])=[CH:7][N:6]=1)(=[O:20])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 59242786HCID 59242786, compound

Product 1

HCID 686973182-Methanesulfonyl-5-methyl-4-pyridin-3-yl-pyrimidineYield 88%

Procedure

A solution of 5-methyl-2-methylsulfanyl-4-pyridin-3-yl-pyrimidine (1.28 g, 5.90 mmol) in MeOH (45 ml) was cooled at 0° C. and then an aqueous solution of oxone (11 g, 17.95 mmol in 45 ml of water) was added dropwise. After 15 minutes, ice bath was removed and the stirring continue for 3 hours. The mixture was neutralized with solid NaHCO3 and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 1.3 g of the title compound as a white powder (88% yield).

Workup

  1. customice bath was removed
  2. waitthe stirring continue for 3 hours
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f33826bba26143329662b10d8da64daa
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

Loading…