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

HRID 440464Notes

Reaction equation

HRID 440464 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-19495a0139054b40990c75db12e9c3bc
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

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