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

HRID 1744296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744296
[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

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-86f3e53568d846b09e3ed991b52be96f
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015226B2

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