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

HRID 1756005Notes

Reaction equation

HRID 1756005 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]([NH: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]([NH: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]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 183578244-Chloro-5-ethoxycarbonyl-6-ethylpyrimidineHCID 224076074-Butylaminophenethylamine

Product 1

HCID 22407600Ethyl 4-(2-(4-butylaminophenyl)ethylamino)-6-ethylpyrimidine-5-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (0.28 g, 2.77 mmol) was added to a solution of ethyl 4-chloro-6-ethylpyrimidine-5-carboxylate (0.30 g, 1.40 mmol) in toluene (10 ml). The mixture was stirred at room temperature. Then, 4-butylaminophenethylamine (0.40 g, 2.08 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-butylaminophenyl)ethylamino)-6-ethylpyrimidine-5-carboxylate (0.30 g, 58%).

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-72423f81b540402e8773fb724df01bb6
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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