Methanol → Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1409588Notes

Reaction equation

HRID 1409588 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12](SC)=[N:11][C:10]=1[C:19]([O:21][CH3:22])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23]O.C(Cl)Cl.O[O:29][S:30]([O-:32])=O.[K+]>O>[CH3:22][O:21][C:19]([C:10]1[N:11]=[C:12]([S:30]([CH3:23])(=[O:32])=[O:29])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 23707502Potassium hydroxy sulfiteHCID 86710286Methyl 5-(benzyloxy)-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 86710287Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1 L round-bottomed flask, methyl 5-(benzyloxy)-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (5.57 g, 17.4 mmol) was combined with MeOH (400 ml) and DCM (50 ml). A solution of oxone (21.4 g, 34.8 mmol) in water (100 ml) was added. The mixture was stirred at room temperature for 5 hours and then evaporated to dryness. The residue was taken up into EtOAc, washed with 3N NaOH aqueous solution, water, and brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound as a white solid (3.7 g; 60%). LCMS: m/z=353 (MH+).

Workup

  1. customevaporated to dryness
  2. washwashed with 3N NaOH aqueous solution, water, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da95aed1b9394042bacf66be36652d97
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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