Diethyl Ether → 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

HRID 1675659Notes

Reaction equation

HRID 1675659 reaction equation
[N:1]([CH2:4][C:5]1[C:10]([CH2:11][CH3:12])=[N:9][C:8]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:7]=2[C:6]=1[NH:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[N+]=[N-].CCOCC>C(O)C.[Pd]>[NH2:1][CH2:4][C:5]1[C:10]([CH2:11][CH3:12])=[N:9][C:8]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:7]=2[C:6]=1[NH:18][CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 596832325-(Azidomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine2×

Product 1

HCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-(azidomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (10.3 g, 34 mmol, e.g. which can be as prepared in Intermediate 6) in ethanol (200 ml) was added to 10% palladium on carbon (1 g) and stirred under an atmosphere of hydrogen for 3 hours at room temperature. The catalyst was removed by filtration under nitrogen and washed well with ethanol. The filtrate was evaporated to dryness to give a dark oil. Ether was added and then evaporated to give the title compound as a foamy semi-solid (9.35 g).

Workup

  1. customThe catalyst was removed by filtration under nitrogen
  2. washwashed well with ethanol
  3. customThe filtrate was evaporated to dryness
  4. customto give a dark oil
  5. customevaporated

Sources & evidence

ORD record
ord-a26fdbd9df8d4b63a89a977bee375f67
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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