(3-Chloropropyl)benzene → 2-Amino-6-(2,6-dichlorophenyl)-8-(3-phenylpropyl)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3233

反応式

HRID 3233 の反応式
[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][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O.C(OCC)(=O)C>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11](=[O:22])[N:10]([CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:8]=2[N:9]=1

参加物

6

反応物 3

HCID 7706(3-Chloropropyl)benzeneHCID 24758Sodium hydrideHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

生成物 1

HCID 116832892-Amino-6-(2,6-dichlorophenyl)-8-(3-phenylpropyl)-8H-pyrido[2,3-d]pyrimidin-7-one収率 57.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a suspension of NaH (60% in mineral oil, 58 mg) in 10 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (320 mg, 1.04 mmol). The mixture was heated to 60° C. resulting in a clear solution. 1-Chloro-3-phenylpropane (260 μL, 1.81 mmol) was added, and the reaction mixture was heated at 60° C. for 35 minutes, then poured onto ice water. The resulting gummy solid was dissolved in ethyl acetate, washed with water, and dried over magnesium sulfate. Filtration, followed by concentration in vacuo, gave an oil that was purified by flash chromatography, eluting with 1:3 hexane:ethyl acetate to provide 345 mg of crude product. Recrystallization from ethyl acetate and hexane followed by drying in vacuo provided 253 mg (57%) of 2-amino-6-(2,6-dichlorophenyl)-8-(3-phenylpropyl)-8H-pyrido[2,3-d]pyrimidin-7-one; mp 161°-163° C.

後処理

  1. customresulting in a clear solution
  2. temperaturethe reaction mixture was heated at 60° C. for 35 minutes
  3. additionpoured onto ice water
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. concentrationfollowed by concentration in vacuo
  8. customgave an oil that
  9. customwas purified by flash chromatography
  10. washeluting with 1:3 hexane
  11. customethyl acetate to provide 345 mg of crude product
  12. customRecrystallization from ethyl acetate and hexane
  13. customby drying in vacuo

出典と根拠

ORDレコード
ord-ce2698e35bd94905bfdf55ec0d5c3c0a
出典データセット
uspto-grants-1998_03
特許番号
US05733914

関連ノート

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