5-[2-Butoxy-5-(2-furyl)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one → 5-(2-Butoxy-5-tetrahydro-2-furanyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354208Notes

Reaction equation

HRID 354208 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([C:12]2[NH:13][C:14](=[O:27])[C:15]3[C:16](=[C:18]([CH2:25][CH3:26])[N:19]([CH2:21][CH2:22][O:23][CH3:24])[N:20]=3)[N:17]=2)=[CH:10][C:9]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[H][H]>C(O)C.[Pd]>[CH2:1]([O:5][C:6]1[C:11]([C:12]2[NH:13][C:14](=[O:27])[C:15]3[C:16](=[C:18]([CH2:25][CH3:26])[N:19]([CH2:21][CH2:22][O:23][CH3:24])[N:20]=3)[N:17]=2)=[CH:10][C:9]([CH:28]2[CH2:32][CH2:31][CH2:30][O:29]2)=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 1363883795-[2-Butoxy-5-(2-furyl)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1357306435-(2-Butoxy-5-tetrahydro-2-furanyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the title compound from example 12 (50 mg, 0.11 mmol) in ethanol (10 ml) was charged with 10% Pd on carbon (15 mg) and stirred at room temperature for 6 h under 60 psi of hydrogen. After removal of the catalyst by filtration, the reaction mixture was concentrated in vacuo and purified by column chromatography (eluting with methylene chloride to 98:2 methylene chloride:methanol) to afford the title compound as a white solid after precipitation from diethyl ether (15 mg, 0.03 mmol).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. custompurified by column chromatography (eluting with methylene chloride to 98:2 methylene chloride:methanol)

Sources & evidence

ORD record
ord-1773656d77c9499e96470dad1dc181f6
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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