Benzene → HCID 178466938, compound

HRID 619184Notes

Reaction equation

HRID 619184 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[CH:17]1([N:22]2[C:26]([NH2:27])=[C:25]([C:28]([NH2:30])=[O:29])[C:24]([CH2:31][CH3:32])=[N:23]2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C1C=CC=CC=1.O>[Pd].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC>[CH:17]1([N:22]2[C:26]3=[N:27][C:6]([C:5]4[CH:8]=[CH:9][C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:11][C:4]=4[O:3][CH2:1][CH3:2])=[N:30][C:28](=[O:29])[C:25]3=[C:24]([CH2:31][CH3:32])[NH:23]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

8

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 9587084-(Diethylamino)-2-ethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178466938HCID 178466938, compoundYield 15.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 2-ethoxy-4-(diethylamino)benzaldehyde (7.87 g, 35.56 mmol), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.95 g, 17.78 mmol), p-toluenesulfonic acid monohydrate (0.05 g), 10% palladium on carbon (0.11 g) and benzene (150 ml) was refluxed overnight with the azeotropic removal of water. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was combined with that from a similar experimental run, and dissolved in CH2Cl2, and loaded onto a silica gel column. Elution of the column with ether/hexane (60/40) afforded a green foam which was titurated with refluxing hexane, and cooled and the product, as pale yellow needles, was collected by filtration to afford 1.19 g (8%) of 1-cyclopentyl-3-ethyl-6-[2-ethoxy-4-(diethylamino)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 138-139° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutiondissolved in CH2Cl2
  4. washElution of the column with ether/hexane (60/40)
  5. customafforded a green foam which
  6. temperaturecooled
  7. filtrationthe product, as pale yellow needles, was collected by filtration

Sources & evidence

ORD record
ord-7d482d272b9042e3b034bf1175e482ee
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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