Water → HCID 22249707, compound

HRID 584831Notes

Reaction equation

HRID 584831 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:20])[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[C:3]=1[CH2:22][CH2:23][CH:24](Cl)[CH2:25][CH2:26][CH3:27].O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:38][O:39][CH2:40][CH2:41][NH2:42]>CN(C)C=O>[CH3:38][O:39][CH2:40][CH2:41][N:42]1[C:2]2[N:7]3[N:8]=[C:9]([CH3:20])[C:10]([C:11]4[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=4[CH3:19])=[C:6]3[N:5]=[C:4]([CH3:21])[C:3]=2[CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 5

HCID 962Water2×HCID 5238Sodium IodideHCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 22249904HCID 22249904, compound

Product 1

HCID 22249707HCID 22249707, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

7-Chloro-6-(3-chlorohexyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidine (170 mg, 0.406 mmol) was dissolved in 2-methoxyethylamine (2 mL), followed by heating under reflux for one hour. Water was added to the reaction mixture, followed by extracting with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated, to give a pale yellow oil. The oil was dissolved in N,N-dimethylformamide (10 mL), and sodium iodide (62 mg, 0.416 mmol) and potassium carbonate (172 mg, 1.25 mmol) were added thereto. The mixture was stirred at 150° C. for two days. After cooling, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then evaporated. The residue was purified by silica gel column chromatography (5-10% ethyl acetate/hexane), to give the title compound (60 mg, 0.143 mmol) as a pale yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for one hour
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto give a pale yellow oil
  8. temperatureAfter cooling
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customevaporated
  13. customThe residue was purified by silica gel column chromatography (5-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4d5d54bdf60542a78fd4f342a01eec11
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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