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

HRID 357482Notes

Reaction equation

HRID 357482 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=S(=O)=O)[C:7]([O:12][CH3:13])=[N:6][C:5](C)=[N:4]1.[OH:15][CH:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:12][CH3:13])[N:6]=[C:5]([O:15][CH:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9855510Methyl 2-hydroxy-3,3-dimethylbutanoateHCID 771347914,6-Dimethoxy-2-methyl-sulfonylpyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.18 g (10.0 mmol) of 4,6-dimethoxy-2-methyl-sulfonylpyrimidine and 1.62 g (11.0 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 60° with stirring. After 3 hours, the solvent was removed in a rotary evaporator at 60° C./20 mbar. The residue was taken up in 40 ml of water and 40 ml of ethyl acetate. After the organic phase had been separated off, the aqueous phase was again extracted with 40 ml of ethyl acetate. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The title product was obtained in a yield of 2.76 g (93.8 percent of theory) in the form of pale yellowish crystals (GC content 96.6 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 40 ml of ethyl acetate
  4. washThe combined organic phases was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-adbef3802671476d8d696eb6b9720bf6
Source dataset
uspto-grants-1998_11
Patent number
US05840892

Reaction notes

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