Benzene → HCID 178437875, compound

HRID 2257020Notes

Reaction equation

HRID 2257020 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C(OC(C[N:27]1[CH:31]=[CH:30][CH:29]=[CH:28]1)=O)C.Cl.[CH:33]1C=CC=C[CH:34]=1>>[CH:1]1([N:6]2[C:10]3=[N:11][C:33]([CH2:34][C:31]4[NH:27][CH:28]=[CH:29][CH:30]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 5

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 350610Ethyl 2-pyrrol-1-ylacetateHCID 16682925TrimethylaluminumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437875HCID 178437875, compound

Procedure

To a solution of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.0 g, 4.5 mmol) in benzene (10 ml) in an ice bath was added trimethylaluminum (4.9 ml, 2M in toluene). The reaction mixture was stirred at room temperature for 1 hour, then 1-(ethoxycarbonylmethyl)pyrrole (0.7 g) in benzene (25 ml) was added and the reaction mixture was refluxed overnight. The reaction mixture was cooled, 2N HCl was added and the mixture was extracted with CHCl3 (3×). The organic layer was separated, dried over MgSO4, and concentrated in vacuo. The residue was digested with ether and recrystallized from ether to afford 1-cyclopentyl-3-ethyl-6-(1-pyrrolylmethyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 170°-172° C.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with CHCl3 (3×)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customrecrystallized from ether

Sources & evidence

ORD record
ord-48d9cac0971a46da9d1e13ba4a5f91d0
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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