Hydrochloric Acid → 6-Cyclopentylmethyl-1-(2,3-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 68933Notes

Reaction equation

HRID 68933 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[CH:18]1([CH2:23][C:24](OC)=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.[H-].[Na+].Cl.[Cl-].[Na+]>C(O)C>[CH:18]1([CH2:23][C:24]2[NH:17][C:15](=[O:16])[C:3]3[CH:4]=[N:5][N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=4[CH3:14])[C:2]=3[N:1]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 121505625-amino-1-(2,3-dimethylphenyl)-1H-pyrazole-4-carboxamideHCID 12512040Methyl 2-cyclopentylacetate

Product 1

HCID 1360351396-Cyclopentylmethyl-1-(2,3-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.1 g (0.43 mmol) of 5-amino-1-(2,3-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 16A) is dissolved under argon in 6 ml of absolute ethanol and 0.24 g (1.7 mmol) of methyl cyclopentylacetate and 0.17 g (4.34 mmol) of 60% sodium hydride (suspension in mineral oil) are added. The reaction mixture is heated to reflux overnight. Cooling to room temperature is followed by acidification with concentrated hydrochloric acid. The mixture of sodium chloride and the product precipitated thereby is filtered off and washed several times with water and diethyl ether. Drying under high vacuum results in 69 mg (49% of theory) of the product as colourless solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe product precipitated
  4. filtrationthereby is filtered off
  5. washwashed several times with water and diethyl ether
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-33c8f8aed65c4703a7f6ae04115d7b0f
Source dataset
uspto-grants-2014_09
Patent number
US08822479B2

Reaction notes

Loading…