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

HRID 3179

反応式

HRID 3179 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][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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db033153fe46420cb6ff2af2382ca19e
出典データセット
uspto-grants-1998_03
特許番号
US05733914

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