Sodium hydride → 8-(2-methoxyethyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300075ノート

反応式

HRID 2300075 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.Br[CH2:22][CH2:23][O:24][CH3:25]>CN(C)C=O>[CH3:25][O:24][CH2:23][CH2:22][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]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 809722-Bromoethyl methyl etherHCID 105140732-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

生成物 1

HCID 53302398-(2-methoxyethyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one収率 56.2%

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 (49 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 (200 mg, 0.84 mmol). The reaction mixture was heated to 50° C. resulting in a yellow solution. The solution was cooled slightly, and 2-bromoethylmethyl ether (140 μL, 1.49 mmol) was added. The reaction mixture was heated at 50° C. for 10 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 a gradient of 2:1 hexane:ethyl acetate to all ethyl acetate gave 140 mg (56%) of 8-(2-methoxyethyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 179-180° C.

後処理

  1. customresulting in a yellow solution
  2. temperatureThe solution was cooled slightly
  3. temperatureThe reaction mixture was heated at 50° C. for 10 minutes
  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 a gradient of 2:1 hexane

出典と根拠

ORDレコード
ord-480047e5858a4d43b32c4c72043d322f
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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