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

HRID 1827932노트

반응식

HRID 1827932 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-b2119943a893406680c78bfa8a7abbac
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07056927B2

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