N,N-Dimethylaniline → HCID 22249888、化合物

HRID 584786ノート

反応式

HRID 584786 の反応式
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[C:8]([CH3:21])=[N:9][N:10]2[C:15](O)=[C:14]([CH2:17][CH2:18]O)[C:13]([CH3:20])=[N:12][C:11]=12.C[N:23](C)[C:24]1[CH:29]=[CH:28]C=[CH:26][CH:25]=1>C(OCC)(=O)C>[Br:6][C:7]1[C:8]([CH3:21])=[N:9][N:10]2[C:15]3[N:23]([CH:24]([CH2:29][CH3:28])[CH2:25][CH3:26])[CH2:18][CH2:17][C:14]=3[C:13]([CH3:20])=[N:12][C:11]=12

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178432037HCID 178432037、化合物

生成物 1

HCID 22249888HCID 22249888、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

Phosphorus oxychloride (3.3 mL) was added to a solution of 3-bromo-6-(2-hydroxyethyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol (1.0 mg, 3.50 mmol) in N,N-dimethyaniline (5 mL), followed by stirring at 120° C. for 20 minutes. After cooling to room temperature, the mixture was added dropwise slowly into ice-water under vigorously stirring. Then, the mixture was stirred for two hours while raising a temperature gradually to room temperature, followed by diluting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. 3-Aminopentane (10 mL) was added to a solution of the residue in acetonitrile (30 mL), followed by heating under reflux for three hours. The mixture was diluted with ethylacetate, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crystals were collected by filtration, to give the title compound (700 mg) as white crystals.

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringunder vigorously stirring
  3. stirringThen, the mixture was stirred for two hours
  4. temperaturewhile raising a temperature gradually to room temperature
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. addition3-Aminopentane (10 mL) was added to a solution of the residue in acetonitrile (30 mL)
  9. temperatureby heating
  10. temperatureunder reflux for three hours
  11. additionThe mixture was diluted with ethylacetate
  12. washthe organic layer was washed with water and brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customevaporated
  15. filtrationThe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-7b124a80daff44fc80e56280c3ba5161
出典データセット
uspto-grants-2005_08
特許番号
US06927221B2

反応ノート

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