Dimethylformamide → Methyl 2-((4,6-Dimethoxypyrimidin-2-yl)oxy)-3-phenoxy-3-phenylbutanoate

HRID 378363Notes

Reaction equation

HRID 378363 reaction equation
[CH2:1]([O:8][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.CN(C=O)C.[H-].[Na+].[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34](S(C)(=O)=O)[N:33]=1>C(O)(=O)C.O>[O:8]([C:9]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH:10]([O:15][C:34]1[N:35]=[C:36]([O:38][CH3:39])[CH:37]=[C:32]([O:31][CH3:30])[N:33]=1)[C:11]([O:13][CH3:14])=[O:12])[C:1]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15292268Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate2×

Product 1

HCID 15766825Methyl 2-((4,6-Dimethoxypyrimidin-2-yl)oxy)-3-phenoxy-3-phenylbutanoateYield 24.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4.4 g (15.4 mmol) of methyl 3-phenoxy-3-phenyl-2-hydroxybutyrate (Compound 1.1) are dissolved in 40 mol of DMF, and 0.46 g (18.4 mmol) of sodium hydride is added. The mixture is stirred for 1 hour and then 3.4 g (15.4 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine are added. The mixture is stirred at room temperature for 24 hours and then cautiously hydrolyzed with 10 mo of water, the pH is adjusted to 5 with acetic acid, and the solvent is removed by distillation under high vacuum. The residue is taken up in 100 mo of ethyl acetate, washed with water, dried over sodium sulfate and distilled to remove solvents. 10 ml of methyl t-butyl ether are added to the residue, and the precipitate is filtered off with suction. Drying results in 1.6 g of a white powder.

Workup

  1. stirringThe mixture is stirred at room temperature for 24 hours
  2. customthe solvent is removed by distillation under high vacuum
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled
  6. customto remove solvents
  7. addition10 ml of methyl t-butyl ether are added to the residue
  8. filtrationthe precipitate is filtered off with suction
  9. customDrying

Sources & evidence

ORD record
ord-ecdb800dff944e338678eaef41724959
Source dataset
uspto-grants-2000_02
Patent number
US06030975

Reaction notes

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