3-Bromopentane → 8-(1-ethylpropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300070노트

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HRID 2300070 반응식
[H-].[Na+].[C:3]1([NH:9][C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:14]=3[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C)C=O>[CH2:23]([CH:22]([N:16]1[C:14]2[N:15]=[C:10]([NH:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:11]=[CH:12][C:13]=2[CH:19]=[CH:18][C:17]1=[O:20])[CH2:25][CH3:26])[CH3:24]

참가 물질

5

반응물 3

HCID 157383-BromopentaneHCID 24758Sodium hydride2회HCID 105140732-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

생성물 1

HCID 98577908-(1-ethylpropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one수율 23%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a suspension of NaH (33 mg of a 60% suspension of NaH in mineral oil) in 7 mL of dimethylformamide was added 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one (154 mg, 0.65 mmol). The reaction mixture was heated to 60° C. resulting in a clear solution. The solution was cooled slightly, and 3-bromopentane (125 μL, 1.01 mmol) was added. The reaction was heated at 60° C. for 30 minutes, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with 1:1 ethyl acetate:hexane to provide 45 mg (23%) of 8-(1-ethylpropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one , mp 116-118° C.

후처리

  1. customresulting in a clear solution
  2. temperatureThe solution was cooled slightly
  3. temperatureThe reaction was heated at 60° C. for 30 minutes
  4. temperaturecooled to room temperature
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-25e3af1be9344ef786132953734ff473
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498163B1

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