Sodium Bicarbonate → 2-Methylsulfonyl-4-benzyloxy-pyrimidine

HRID 19667Notes

Reaction equation

HRID 19667 reaction equation
CS[C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1.O[O:18][S:19]([O-:21])=O.[K+].[C:23]([O-])(O)=O.[Na+]>C1COCC1.CO.O>[CH3:23][S:19]([C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1)(=[O:21])=[O:18]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 111838682-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(methylthio)-4-[(phenylmethyl)oxy]pyrimidine (P9, 245 mg) in THF/MeOH 1/1 (15.6 mL) was added a solution of Oxone® (2.6 g) in water (14 mL). After 40 min a saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with dichloromethane/methanol from 100/0 to 99/1 to give the title compound as a white solid (230 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by a silica SPE cartridge (10 g)
  7. washeluting with dichloromethane/methanol from 100/0 to 99/1

Sources & evidence

ORD record
ord-6ed28fddb3784930a872ce9efc7b88b1
Source dataset
uspto-grants-2010_06
Patent number
US07745458B2

Reaction notes

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