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

HRID 1784063Notes

Reaction equation

HRID 1784063 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[O:17])[CH:10]=[CH:11][CH:12]=1.Cl.O.C[CH2:22][OH:23]>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][N:15]2[C:2](=[O:3])[CH2:1][C:22](=[O:23])[NH:18][C:16]2=[O:17])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol3×HCID 962WaterHCID 2723922Sodium ethoxideHCID 3052719Urea, (3-methoxyphenethyl)-2×

Product 1

HCID 575910951-[2-(3-Methoxyphenyl)ethyl]pyrimidine-2,4,6(1H,3H,5H)-trioneYield 74%

Procedure

To a solution of NaOEt (144 mmol, fleshly prepared from 3.3 g of Na) in EtOH (80 mL), a solution of ethyl malonate (2) (22 mL, 144 mmol) in EtOH (250 mL) was added. The mixture was refluxed then added a solution of [2-(3-methoxy-phenyl)-ethyl]-urea (2) (23.3 g, 120 mmol) in EtOH (300 mL). The reaction mixture was refluxed overnight, then cooled to room temperature. The mixture was acidified carefully with 1M HCl aq. then poured into water (1 L). The precipitate which was formed was collected by filtration, washed with water then dried under reduced pressure to give the title compound (23.2 g, 74%). MS (ESI) (M+H)+ 263.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe reaction mixture was refluxed overnight
  3. customThe precipitate which was formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-9f43836919cc44168d960ef77667b36f
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

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