N,N-Dimethylaniline → Ethyl 4-(7-(butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)butanoate

HRID 890181Notes

Reaction equation

HRID 890181 reaction equation
O(Cl)Cl.CN(C)[C:6]1[CH:11]=CC=[CH:8][CH:7]=1.[C:13]1([CH3:41])[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1[C:21]1[C:22]([CH3:40])=[N:23][N:24]2[C:29](=O)[C:28]([CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:27]([CH3:39])[NH:26][C:25]=12.C(=O)([O-])[O-].[K+].[K+].C(N)CCC>C(#N)C.O>[CH2:11]([C:29]1[N:24]2[N:23]=[C:22]([CH3:40])[C:21]([C:14]3[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[CH3:41])=[C:25]2[N:26]=[C:27]([CH3:39])[C:28]=1[CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 5

HCID 949N,N-DimethylanilineHCID 8007ButylamineHCID 11430Potassium Carbonate2×HCID 24646Chlorine monoxideHCID 178471269HCID 178471269, compound

Product 1

HCID 22249666Ethyl 4-(7-(butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)butanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Phosphoeus oxychloride (11.3 g) and N,N-dimethylaniline (3 droplets) were added to ethyl 4-(3-mesityl-2,5-dimethyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)butanoate (700 mg, 1.77 mmol), followed by heating under reflux for 1.5 hours. After the reaction, it was treated with ice-water, neutralized with potassium carbonate, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The resulting reaction residue was dissolved in acetonitrile (5 ml) and n-butylamine (2 mL) was added, followed by heating under reflux for six hours. After the reaction, it was treated with water, and then neutralized with potassium carbonate, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-25% ethyl acetate/hexane), to give the title compound (2.5 g) as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. customAfter the reaction, it
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe resulting reaction residue
  8. temperatureby heating
  9. temperatureunder reflux for six hours
  10. customAfter the reaction, it
  11. extractionextracted with ethyl acetate
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customevaporated
  14. customThe residue was purified by silica gel column chromatography (10-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7da826292c13472db7a44b69eb27b86a
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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