Urea → 5-(2-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

HRID 28505Notes

Reaction equation

HRID 28505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:13]N(C)C)[C:9](OC)=[O:10].[NH2:17][C:18]([NH2:20])=[O:19].[Na+].[I-].C[Si](Cl)(C)C.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:10])[NH:17][C:18](=[O:19])[NH:20][CH:13]=1

Participants

7

Reactant 5

HCID 1176UreaHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 67505122Methyl 2-(2-chlorophenyl)-3-(dimethylamino)acrylate

Product 1

HCID 220644855-(2-chlorophenyl)pyrimidine-2,4(1H,3H)-dioneYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl 2-(2-chlorophenyl)-3-(dimethylamino)acrylate 6b (0.26 g, 1.08 mmol), urea (0.2 g, 3.26 mmol) and NaI (0.49 g, 3.26 mmol) in acetonitrile (5 mL) was added TMSCl (0.41 mL, 3.26 mmol). The resulting mixture was refluxed for 16 hours, cooled to room temperature, and 1.0 M NaOH (8 mL) was added. The resultant solution was stirred for 20 hr, and acetonitrile was removed in vacuo. The aq. solution was washed with ether, cooled in ice bath, and neutralized with 1 N HCl (8 mL). The precipitate was filtered, washed with additional H2O, and dried to give 5-(2-chlorophenyl)pyrimidine-2,4(1H,3H)-dione 6c (0.16 g, 66%) as a white solid. MS (CI) m/z 222.9, 224.9 (MH+).

Workup

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. customacetonitrile was removed in vacuo
  3. washThe aq. solution was washed with ether
  4. temperaturecooled in ice bath
  5. filtrationThe precipitate was filtered
  6. washwashed with additional H2O
  7. customdried

Sources & evidence

ORD record
ord-87a35943d460418ea8f022473784260a
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Reaction notes

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