Dimethylformamide → 2-(4-Methoxy-6-methyl-2-pyrimidinyloxy)-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionic Acid

HRID 433928Notes

Reaction equation

HRID 433928 reaction equation
[OH:1][CH:2]([C:6]([O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].CN(C=O)C.[H-].[Na+].[CH3:39][O:40][C:41]1[CH:46]=[C:45]([CH3:47])[N:44]=[C:43](S(C)(=O)=O)[N:42]=1>O>[CH3:39][O:40][C:41]1[CH:46]=[C:45]([CH3:47])[N:44]=[C:43]([O:1][CH:2]([C:6]([O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]([OH:5])=[O:4])[N:42]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27723804-Methoxy-6-methyl-2-(methylsulfonyl)pyrimidineHCID 111226872-Hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionic Acid

Product 1

HCID 107688972-(4-Methoxy-6-methyl-2-pyrimidinyloxy)-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionic AcidYield 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g (2.3 mmol) of 2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-diphenylpropionic acid was introduced into 10 ml of DMF, and 340 mg of NaH (50% suspension) were added. After the mixture had been stirred for 15 minutes, 526 mg of 4-methoxy-6-methyl-2-methylsulfonylpyrimidine were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the mixture, which was then extracted with ether. The aqueous phase was acidified with 1 N aqueous HCl, extracted with ether and dried over magnesium sulfate. The solvent was distilled off, the residue was purified by MPLC, and 655 mg (52%) of colorless powder were isolated after recrystallization from ether/n-hexane.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionwas then extracted with ether
  4. extractionextracted with ether
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by MPLC

Sources & evidence

ORD record
ord-d3e7f3054765497a92eb5ce5c9f36687
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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