Water → HCID 86748878, compound

HRID 1756013Notes

Reaction equation

HRID 1756013 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[S:16])=[C:13]([CH2:20][CH3:21])[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:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[S:16])=[C:13]([CH2:20][CH3:21])[N:12]=[C:11]([CH3:22])[N:10]=2)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 86748879HCID 86748879, 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-6-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-27f260803d1c4f958ab9737abb8a85b7
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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