N,N-Dimethylaniline → HCID 22249888, compound

HRID 890171Notes

Reaction equation

HRID 890171 reaction equation
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

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178432037HCID 178432037, compound

Product 1

HCID 22249888HCID 22249888, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8d215074b7ce46098bb4ea7cbaad5485
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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