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Water → Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate

HRID 51998
Notes
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Reaction equation

HRID 51998 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:8][C:7]2=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]([OH:13])=[CH:11][CH:12]=[C:6]2[O:5]1)[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22](S(C)(=O)=O)[N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([O:13][C:10]2[C:9]([C:14]([O:16][CH3:17])=[O:15])=[C:7]3[CH2:8][CH:4]([O:3][CH2:1][CH3:2])[O:5][C:6]3=[CH:12][CH:11]=2)[N:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19077264Methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate

Product 1

HCID 19962778Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylateYield 95%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture comprising 1.0 g of methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate, 1.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.78 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 100° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.5 g (yield: 95%) of the desired compound.

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationIt was concentrated under reduced pressure
  7. customthe oily substance thereby obtained
  8. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-877c567981af4e73ad343d16d8173690
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616537

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes