Water → Ethyl 4-(1-(4-butoxyphenyl)-1-propylamino)-6-ethylpyrimidine-5-carboxylate

HRID 440458Notes

Reaction equation

HRID 440458 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]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]([NH2:36])[CH2:34][CH3:35])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].O>C1(C)C=CC=CC=1>[CH2:22]([O:26][C:27]1[CH:28]=[CH:29][C:30]([CH:33]([NH:36][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)[CH2:34][CH3:35])=[CH:31][CH:32]=1)[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 167925431-(4-Butoxyphenyl)-1-propylamineHCID 183578244-Chloro-5-ethoxycarbonyl-6-ethylpyrimidine

Product 1

HCID 54461306Ethyl 4-(1-(4-butoxyphenyl)-1-propylamino)-6-ethylpyrimidine-5-carboxylateYield 44.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (0.33 g, 3.26 mmol) was added to a solution of ethyl 4-chloro-6-ethylpyrimidine-5-carboxylate (0.40 g, 1.86 mmol) in toluene (10 ml). The mixture was stirred at room temperature. Then, 1-(4-butoxyphenyl)-1-propylamine (0.46 g, 2.22 mmol) was added. After stirring at 80° C. for 3 hours, 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 (=8/2) to give The desired ethyl 4-(1-(4-butoxyphenyl)-1-propylamino)-6-ethylpyrimidine-5-carboxylate (0.32 g, 44%).

Workup

  1. stirringAfter stirring at 80° C. 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-508d8c7694964ac3a9be9608f6fa56d8
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

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