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

HRID 28510Notes

Reaction equation

HRID 28510 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 7d (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 aqueous 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 7e (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 aqueous 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-e32cd6c372a24a87b4af6cb48a69a765
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Reaction notes

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