Potassium Carbonate → Methyl (+/-)-2-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate

HRID 357481Notes

Reaction equation

HRID 357481 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5](S(C2C=CC(C)=CC=2)(=O)=O)[N:4]=1.[OH:21][CH:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:21][CH:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([O:25][CH3:26])=[O:24])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9855510Methyl 2-hydroxy-3,3-dimethylbutanoateHCID 155266204,6-Dimethoxy-2-(4-toluenesulfonyl)pyrimidine

Product 1

HCID 11011508Methyl (+/-)-2-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.94 g (10.0 mmol) of 4,6-dimethoxy-2-(p-toluenesulfonyl)pyrimidine and 1.55 g (10.5 mmol) of methyl (+/-)-2-hydroxy-3,3-dimethylbutanoate were heated in the presence of 2.07 g (15.0 mmol) of potassium carbonate in 20 ml of N,N-dimethylformamide to 100° C. with stirring. After 5 hours, the solvent was removed in a rotary evaporator at 60° C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated. The title product was obtained in a yield of 2.30 g (80.9 percent of theory) in the form of yellowish crystals (GC content 100 percent).

Workup

  1. customthe solvent was removed in a rotary evaporator at 60° C./20 mbar
  2. customAfter the organic phase had been separated off
  3. extractionthe aqueous phase was again extracted with 20 ml of dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-dcf971f7d3ad4490a86fae6d17d12e25
Source dataset
uspto-grants-1998_11
Patent number
US05840892

Reaction notes

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