Water → HCID 86748878, compound

HRID 440466Notes

Reaction equation

HRID 440466 reaction equation
[CH2:1](N(CC)CC)[CH3:2].Cl[CH:9]1[C:14](CC)([C:15]([O:17][CH2:18][CH3:19])=[S:16])[CH:13]=[N:12][C:11]([CH3:22])=[N:10]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:28][CH2:29][NH2:30].O>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:28][CH2:29][NH:30][C:13]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[S:16])=[C:9]([CH2:1][CH3:2])[N:10]=[C:11]([CH3:22])[N:12]=2)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 86749495HCID 86749495, compound

Product 1

HCID 86748878HCID 86748878, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (0.17 g, 1.68 mmol) was added to a solution of ethyl 4-chloro-5-ethyl-2-methylthiopyrimidine-5-carboxylate (0.21 g, 0.81 mmol) in toluene (4 ml), followed by addition of 3,4-dimethoxyphenethylamine (0.18 g, 0.99 mmol). The mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into water, extracted with ethyl acetate 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-(3,4-dimethoxyphenyl)ethylamino)-6-ethyl-2-methylthiopyrimidine-5-carboxylate (0.16 g, 49%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2 )

Sources & evidence

ORD record
ord-5d14f102c5cd442dad426bbeac689400
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

Loading…