HCID 136391022, compound → HCID 66584830, compound

HRID 2369008Notes

Reaction equation

HRID 2369008 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17](=[N:19]O)[CH3:18])[CH:9]=1.[H][H]>[Pd].CCO.CC(O)=O>[NH2:19][CH:17]([C:10]1[CH:9]=[C:8]([N:7]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:29])([CH3:1])[CH3:30])[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=1)[CH3:18]

Participants

5

Reactant 2

HCID 136391022HCID 136391022, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66584830HCID 66584830, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of 1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)pyrazolo[1,5-a]pyrimidin-5-yl]ethanone oxime (4.50 g, 8.77 mmol) in 4:1 EtOH/AcOH (90 mL) under nitrogen in a Parr bottle was treated with 10% Pd on carbon (933 mg, 0.877 mmol), and the mixture was shaken on the Parr apparatus under 45 psi hydrogen for 23 h. The catalyst was removed by filtration through Celite, and the filtrate was concentrated under reduced pressure, azeotroping with toluene at 40-45° C. to remove most AcOH. The oily residue was taken up in EtOAc (˜100 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure to give the title compound, 5-(1-aminoethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (4.02 g, 91% purity, 95% yield) as an oil: MS (ESI+) for C20H39N5O2Si2 m/z 438 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customazeotroping with toluene at 40-45° C.
  4. customto remove most AcOH
  5. washwashed with saturated aqueous NaHCO3 (2×50 mL) and brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e6581b27b5043a19ab953ef5a61a3a9
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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