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

HRID 440459
Notes
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Reaction equation

HRID 440459 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][CH3:21])[N:12]=[CH:11][N:10]=1.[CH2:22]([S:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31][CH2:32][NH2:33])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].O>C1(C)C=CC=CC=1>[CH2:22]([S:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][CH2:32][NH:33][C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][CH3:21])[N:12]=[CH:11][N:10]=2)=[CH:34][CH:35]=1)[CH2:23][CH2:24][CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 183578244-Chloro-5-ethoxycarbonyl-6-ethylpyrimidineHCID 224075954-Butylthiophenethylamine

Product 1

HCID 54522122Ethyl 4-(2-(4-butylthiophenyl)ethylamino)-6-ethylpyrimidine-5-carboxylateYield 55.5%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

Triethylamine (0.19 g, 1.88 mmol) was added to a solution of ethyl 4-chloro-6-ethylpyrimidine-5-carboxylate (0.20 g, 0.93 mmol) in toluene (4 ml). The mixture was stirred at room temperature. Then, 4-butylthiophenethylamine (0.20 g, 0.96 mmol) was added. After stirring for 3 hours, water (20 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 (=8/2 ) to give the desired ethyl 4-(2-(4 -butylthiophenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (0.20 g, 55%).

Workup

  1. stirringAfter stirring for 3 hours
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2 )

Sources & evidence

ORD record
ord-05017d37d7c347259ae6a701d65060df
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05519139

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes