Sodium Hydroxide → Ethyl 4-(2-(4-(2-methylsulfinylethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate

HRID 1756011Notes

Reaction equation

HRID 1756011 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH2:25][CH3:26])[N:17]=[CH:16][N:15]=2)=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:35])C=1.[OH-].[Na+]>C(Cl)Cl>[CH3:1][S:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH2:25][CH3:26])[N:17]=[CH:16][N:15]=2)=[CH:7][CH:6]=1)=[O:35]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 22407590HCID 22407590, compound

Product 1

HCID 22407591Ethyl 4-(2-(4-(2-methylsulfinylethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-(2-(4-(2-methylthioethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (0.25 g, 0.67 mmol) in methylene chloride (20 ml) was stirred under ice-cooling. 80% m-Chloroperbenzoic acid (0.16 g, 0.74 mmol) was added to the solution. The mixture was stirred under ice-cooling for 20 minutes, and then a 1N aqueous solution (20 ml) of sodium hydroxide was added. The mixture was extracted with methylene chloride and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (=8/2) to give the desired ethyl 4-(2-(4-(2-methylsulfinylethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (0.20 g, 77%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (=8/2)

Sources & evidence

ORD record
ord-66a15fb51d844d539aa1266d69ac1ba2
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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