Methyl chloroacetate → methyl 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]acetate

HRID 3179

반응식

HRID 3179 반응식
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[NH:10][C:8]=2[N:9]=1.Cl[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C)C=O>[CH3:28][O:27][C:25](=[O:26])[CH2:24][N:10]1[C:8]2[N:9]=[C:4]([NH2:3])[N:5]=[CH:6][C:7]=2[CH:13]=[C:12]([C:14]2[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=2[Cl:20])[C:11]1=[O:22]

참가 물질

5

반응물 3

HCID 7295Methyl chloroacetateHCID 24758Sodium hydrideHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

생성물 1

HCID 5328629methyl 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]acetate수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a suspension of NaH (60% in mineral oil, 38 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (203 mg, 0.66 mmol). The mixture was heated at 50° C. for 40 minutes resulting in a clear solution. Methyl chloroacetate (90 μL, 1.03 mmol) was added, and the solution was heated at 50° C. for 20 minutes, then cooled to room temperature and poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The aqueous filtrate was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate, filtered, and concentrated. The solids were combined and purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to all ethyl acetate to provide 152 mg (61%) of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid methyl ester; mp 188°-190° C.

후처리

  1. customresulting in a clear solution
  2. temperaturethe solution was heated at 50° C. for 20 minutes
  3. temperaturecooled to room temperature
  4. customThe resulting precipitate was removed by filtration
  5. washwashed with water
  6. extractionThe aqueous filtrate was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography
  11. washeluting with a gradient of 1:1 hexane

출처 및 근거

ORD 기록
ord-db033153fe46420cb6ff2af2382ca19e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733914

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