HCID 86602404, compound → HCID 69184753, compound

HRID 2373221Notes

Reaction equation

HRID 2373221 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]>CCO.[Pt]=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][O:27][CH3:28])=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 86602404HCID 86602404, compound

Product 1

HCID 69184753HCID 69184753, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (2E)-3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylate (50 mg) in EtOH (3 ml) was hydrogenated (3 atm) over platinum oxide (25 mg) at room temperature for 7 hours. The catalyst was filtered off through celite pad and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography-on silica gel eluting with a mixture of EtOAc and n-hexane (1:1) then a mixture of MeOH and CHCl3 (1:40) to give ethyl 3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (29 mg) as a colorless crystal.

Workup

  1. customat room temperature
  2. customfor 7 hours
  3. filtrationThe catalyst was filtered off through celite pad
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography-on silica gel eluting with a mixture of EtOAc and n-hexane (1:1)
  6. additiona mixture of MeOH and CHCl3 (1:40)

Sources & evidence

ORD record
ord-b171c803ce9343c7a251007ccbc1cc31
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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