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

HRID 433932Notes

Reaction equation

HRID 433932 reaction equation
[OH:1][CH:2]([C:6]([O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1)([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].CN(C=O)C.[H-].[Na+].[CH3:43][O:44][C:45]1[CH:50]=[C:49]([CH3:51])[N:48]=[C:47](S(C)(=O)=O)[N:46]=1>O>[CH3:43][O:44][C:45]1[CH:50]=[C:49]([CH3:51])[N:48]=[C:47]([O:1][CH:2]([C:6]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=2)[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=2)[C:3]([OH:5])=[O:4])[N:46]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27723804-Methoxy-6-methyl-2-(methylsulfonyl)pyrimidineHCID 105526572-Hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-di(4-ethylphenyl)propionic Acid

Product 1

HCID 107698872-(4-Methoxy-6-methyl-2-pyrimidinyloxy)-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-di(4-ethylphenyl)propionic AcidYield 23.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.8 g (3.8 mmol) of 2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethoxy)-3,3-di(4-ethylphenyl)propionic acid were introduced into 20 ml of DMF, and 554 mg of NaH (50% suspension) were added. After the mixture had stirred for 15 minutes, 855 mg (4.2 mmol) 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 and 540 mg (23%) 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

Sources & evidence

ORD record
ord-34ddc015546a479e91c6924099ca610c
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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