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

HRID 2054528Notes

Reaction equation

HRID 2054528 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10](=[CH:16]N(C)C)[C:11](OCC)=[O:12].[NH2:20][C:21]([NH2:23])=[O:22].[Na+].[I-].C[Si](Cl)(C)C.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11](=[O:12])[NH:20][C:21](=[O:22])[NH:23][CH:16]=1

Participants

7

Reactant 5

HCID 1176UreaHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 76539495Ethyl 2-(2-chloro-3-methoxyphenyl)-3-(dimethylamino)acrylate

Product 1

HCID 220378355-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of ethyl 2-(2-chloro-3-methoxyphenyl)-3-(dimethylamino)acrylate 3d (1.7 g, 6 mmol), urea (1.08 g, 18 mmol) and NaI (2.7 g, 18 mmol) in acetonitrile (20 mL) was added TMSCl (2.3 mL, 18 mmol). The resulting mixture was refluxed for 16 hours, cooled to room temperature, and 1.0 M NaOH (30 mL) was added. The resultant solution was stirred for 20 hours, and acetonitrile was removed in vacuo. The aq. solution was washed with ether, cooled in ice bath, and neutralized with 1 N HCl (30 mL). The precipitate was filtered, washed with additional H2O, and dried to give 5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione 3e (1.24 g, 82%) as a pale yellow solid. MS (CI) m/z 253.1, 255.1 (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-257c123778ad4e09b85276579ff827b6
Source dataset
uspto-grants-2008_02
Patent number
US07329669B2

Reaction notes

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