Iodoethane → 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3175

反応式

HRID 3175 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]([OH:22])=[N:10][C:8]=2[N:9]=1.[CH2:23](I)[CH3:24]>CN(C)C=O>[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])[N:10]([CH2:23][CH3:24])[C:8]=2[N:9]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178418283HCID 178418283、化合物

生成物 1

HCID 53286252-amino-6-(2,6-dichlorophenyl)-8-ethyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one収率 55.4%

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, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (172 mg, 0.56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodide (60 μL, 0.75 mmol) was added, and the solution was stirred at 50° C. for 3.5 hours, cooled to room temperature, and poured into 30 mL of ice water. The resulting precipitate was removed by filtration and partitioned between ethyl acetate and water. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography, eluting with ethyl acetate, provided 104 mg (55%) of 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 207°-209° C.

後処理

  1. customresulting in a clear solution
  2. temperaturecooled to room temperature
  3. customThe resulting precipitate was removed by filtration
  4. custompartitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash chromatography, eluting with ethyl acetate

出典と根拠

ORDレコード
ord-dc089cf7000c4b12a70b5ffd130e6b36
出典データセット
uspto-grants-1998_03
特許番号
US05733914

関連ノート

読み込み中…