Water → Ethyl 4-(2-(4-(2-methylsulfonyloxyethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate

HRID 440462Notes

Reaction equation

HRID 440462 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][C:20]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH2:31][CH3:32])[N:23]=[CH:22][N:21]=2)=[CH:13][CH:12]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>C(Cl)Cl>[CH3:33][S:34]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][C:20]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH2:31][CH3:32])[N:23]=[CH:22][N:21]=2)=[CH:13][CH:12]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22407599HCID 22407599, compound

Product 1

HCID 22407588Ethyl 4-(2-(4-(2-methylsulfonyloxyethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.88 g, 8.70 mmol) was added to a solution of ethyl 4-(2-(4-(2-hydroxyethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (1.50 g, 4.37 mmol) in methylene chloride (40 ml). The mixture was stirred under ice-cooling, and methanesulfonyl chloride (0.60 g, 5.24 mmol) was added dropwise to the mixture. The resulting mixture was stirred under ice-cooling for 10 minutes after the addition. Then, water (40 ml) was added to the reaction mixture. 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 n-hexane/ethyl acetate (=1/1) to give the desired ethyl 4-(2-(4-(2-methylsulfonyloxyethyl)phenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (1.80 g, 98%).

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred under ice-
  3. temperaturecooling for 10 minutes
  4. additionafter the addition
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=1/1)

Sources & evidence

ORD record
ord-9f147ff0a7944118b61d1980638fe26a
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

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