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

HRID 237889Notes

Reaction equation

HRID 237889 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][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>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[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=4[CH3:14])[C:2]=3[N:1]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 121505615-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamideHCID 12512040Methyl 2-cyclopentylacetate

Product 1

HCID 1360351316-Cyclopentylmethyl-1-(2,6-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-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 15A) 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 sodium chloride precipitated thereby is filtered off. The filtrate is concentrated in vacuo, and the remaining residue is purified by preparative HPLC(YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 74 mg (53% of theory) of the product are obtained as a colourless solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customThe sodium chloride precipitated
  4. filtrationthereby is filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe remaining residue is purified by preparative HPLC(YMC Gel ODS-AQ S 5/15 μm
  7. custom0 min 30% B, 5 min 30% B, 50 min 95% B
  8. custom74 mg (53% of theory) of the product are obtained as a colourless solid

Sources & evidence

ORD record
ord-413943c4f66f4735a2a70a6a087bb516
Source dataset
uspto-grants-2014_02
Patent number
US08642605B2

Reaction notes

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