Pyridine → HCID 9821437, compound

HRID 725820Notes

Reaction equation

HRID 725820 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]=1.N1C=CC=CC=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27].C(=O)([O-])O.[Na+]>ClCCl>[CH2:11]([C:4]1[CH:3]=[C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:24]=[C:23]([O:22][CH3:21])[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=2)[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 19709702HCID 19709702, compound

Product 1

HCID 9821437HCID 9821437, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Amino-5-n-butylpyrazolo[1,5-a]pyrimidine (1.90 g) and pyridine (20 ml) were dissolved in 20 ml of dry dichloromethane. A dry dichloromethane solution (10 ml) containing 2.6 g of 3,4,5-trimethoxybenzoyl chloride was slowly added dropwise thereto and stirred at room temperature for 10 hours. After addition of 50 ml of a 10% aqueous sodium hydrogen carbonate solution, the reaction mixture was extracted with chloroform. The organic layer was collected, washed with 10% aqueous hydrochloric acid and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:2) and recrystallized from diethyl ether-n-hexane to provide 2.4 g of the object compound as colorless crystals. Table 1 shows the structure and melting point of the compound obtained.

Workup

  1. additionwas slowly added dropwise
  2. extractionthe reaction mixture was extracted with chloroform
  3. customThe organic layer was collected
  4. washwashed with 10% aqueous hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:2)
  8. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-6fba48b8aa274efd880cd3e96e73eb9c
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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