Triethylamine → HCID 19608373, compound

HRID 725824Notes

Reaction equation

HRID 725824 reaction equation
P(Cl)(Cl)([Cl:3])=O.C(N(CC)CC)C.[C:13]([O:16][CH:17]([CH3:30])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24](O)[N:23]2[N:27]=[CH:28][CH:29]=[C:22]2[N:21]=1)(=[O:15])[CH3:14]>C1(C)C=CC=CC=1>[C:13]([O:16][CH:17]([CH3:30])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([Cl:3])[N:23]2[N:27]=[CH:28][CH:29]=[C:22]2[N:21]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178476213HCID 178476213, compound

Product 1

HCID 19608373HCID 19608373, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus oxychloride (6.4 ml) and triethylamine (3.5 ml) were added to 40 ml of a toluene suspension containing 4.2 g of the crystals obtained in step (4), and the mixture was refluxed with heating for 6 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was poured into ice water. The mixture was neutralized with sodium acetate and extracted with ethyl acetate. The organic layer was collected, washed with a saturated saline solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=4:1) to provide 4.3 g of 5-(3-acetoxybutyl)-7-chloropyrazolo[1,5-a]pyrimidine as a light yellow oily compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 6 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionthe residue was poured into ice water
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was collected
  8. washwashed with a saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=4:1)

Sources & evidence

ORD record
ord-ba7049856d4a464c956dd7bcb8b22899
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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