Ethyl Acetate → 4-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-ylmethyl]-benzoic acid methyl ester

HRID 3229

反応式

HRID 3229 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.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)=[O:26].C(OCC)(=O)C>CN(C)C=O>[CH3:23][O:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:10]2[C:8]3[N:9]=[C:4]([NH2:3])[N:5]=[CH:6][C:7]=3[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11]2=[O:22])=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

生成物 1

HCID 115034214-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-ylmethyl]-benzoic acid methyl ester収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of NaH (60% in mineral oil, 36 mg) in 7 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (195 mg, 0.64 mmol). The mixture was heated at 40° C. to 50° C. for 20 minutes, resulting in a clear solution. Methyl 4-(bromomethyl) benzoate (206 mg, 0.90 mmol) was added, and the reaction mixture was heated at 40° C. to 50° C. for 15 minutes, then poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The solid was purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to 1:2 hexane: ethyl acetate, then dried in vacuo to provide 204 mg of 4-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-ylmethyl]-benzoic acid methyl ester containing 0.16 equivalents of ethyl acetate; mp 235°-237° C.

後処理

  1. temperatureThe mixture was heated at 40° C. to 50° C. for 20 minutes
  2. customresulting in a clear solution
  3. temperaturethe reaction mixture was heated at 40° C. to 50° C. for 15 minutes
  4. customThe resulting precipitate was removed by filtration
  5. washwashed with water
  6. customThe solid was purified by flash chromatography
  7. washeluting with a gradient of 1:1 hexane
  8. dry with materialethyl acetate to 1:2 hexane: ethyl acetate, then dried in vacuo

出典と根拠

ORDレコード
ord-145f75e858214880a64bbd4992e3190e
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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