2-Iodobutane → 8-sec-Butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300074ノート

反応式

HRID 2300074 の反応式
[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.I[CH:22]([CH2:24][CH3:25])[CH3:23]>CN(C)C=O>[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])([CH2:24][CH3:25])[CH3:23]

参加物

5

反応物 3

HCID 105592-IodobutaneHCID 24758Sodium hydride2 回HCID 105140732-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

生成物 1

HCID 53302278-sec-Butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one収率 12%

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 (47 mg of a 60% suspension of NaH in mineral oil) in 6 mL of dimethylformamide was added 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one (202 mg, 0.85 mmol). The reaction mixture was heated to 50° C. to 60° C. resulting in a yellow solution. The solution was cooled slightly, and 2-iodobutane (140 μL, 1.22 mmol) was added. The reaction was heated at 50° C. for 20 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. Purification by flash chromatography eluting with 2:1 ethyl acetate:hexane gave 29 mg (12%) of 8-sec-butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 155-156° C.

後処理

  1. temperatureThe reaction mixture was heated to 50° C. to 60° C.
  2. customresulting in a yellow solution
  3. temperatureThe solution was cooled slightly
  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. customPurification by flash chromatography
  10. washeluting with 2:1 ethyl acetate

出典と根拠

ORDレコード
ord-f06ff9445277496eade8ac29d9c4c1cd
出典データセット
uspto-grants-2002_12
特許番号
US06498163B1

反応ノート

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