Urea, (3-methoxyphenethyl)- → 1-[2-(3-Methoxyphenyl)ethyl]pyrimidine-2,4,6(1H,3H,5H)-trione

HRID 1773298Notes

Reaction equation

HRID 1773298 reaction equation
[Na].[C:2]([O:8]CC)(=O)[CH2:3][C:4]([O-:6])=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH:21][C:22]([NH2:24])=[O:23])[CH:16]=[CH:17][CH:18]=1>CCO>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][N:21]2[C:2](=[O:8])[CH2:3][C:4](=[O:6])[NH:24][C:22]2=[O:23])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3052719Urea, (3-methoxyphenethyl)-HCID 3595298Propanedioic acid, monoethyl esterHCID 5360545Sodium

Product 1

HCID 575910951-[2-(3-Methoxyphenyl)ethyl]pyrimidine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (236 mg, 10.2 mmol, 2 eq.) was added to degassed EtOH (18 mL), when sodium dissolved completely, ethyl malonate (1.56 mL, 10.2 mmol, 2 eq.) was added and the reaction was refluxed for 1 h. Intermediate 1 (995 mg, 5.12 mmol, 1 eq.) in EtOH (4 mL) was then added and the reaction was refluxed for 1 day. The desired intermediate 37 1-[2-(3-methoxy-phenyl)-ethyl]-pyrimidine-2,4,6-trione precipitated upon addition of 2N aqueous HCl, it was filtered and washed with H2O and finally dried.

Workup

  1. customto degassed EtOH (18 mL), when sodium
  2. dissolutiondissolved completely
  3. temperaturethe reaction was refluxed for 1 h
  4. temperaturethe reaction was refluxed for 1 day
  5. customThe desired intermediate 37 1-[2-(3-methoxy-phenyl)-ethyl]-pyrimidine-2,4,6-trione precipitated upon addition of 2N aqueous HCl, it
  6. filtrationwas filtered
  7. washwashed with H2O
  8. customfinally dried

Sources & evidence

ORD record
ord-dc0df237194c468a97258c5f293bcd2a
Source dataset
uspto-grants-2016_02
Patent number
US09255095B2

Reaction notes

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