Benzyl 3-(3-chloropyrazin-2-yloxy)azetidine-1-carboxylate → 2-(Azetidin-3-yloxy)pyrazine

HRID 454902Notes

Reaction equation

HRID 454902 reaction equation
Cl[C:2]1[C:3]([O:8][CH:9]2[CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10]2)=[N:4][CH:5]=[CH:6][N:7]=1>[Pd].CCO>[NH:11]1[CH2:10][CH:9]([O:8][C:3]2[CH:2]=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:12]1

Participants

4

Reactant 1

HCID 58547798Benzyl 3-(3-chloropyrazin-2-yloxy)azetidine-1-carboxylate

Product 1

HCID 585479842-(Azetidin-3-yloxy)pyrazineYield 181%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a nitrogen-purged round bottomed flask was added benzyl 3-(3-chloropyrazin-2-yloxy)azetidine-1-carboxylate (see PREPARATION P20.1; 0.400 g, 0.688 mmol) and Pd/C (0.10 g, 0.094 mmol) and EtOH (10 mL). Hydrogen gas was bubbled through the solution for 1 minute, then a balloon of hydrogen gas was placed atop the round bottomed flask. After 30 minutes, the balloon was removed and the round bottomed flask sealed with a rubber septum. After 16 hours, the reaction was filtered through CELITE® and the cake was washed liberally with EtOAc. The filtrate was concentrated in vacuo to give crude 2-(azetidin-3-yloxy)pyrazine (0.188 g, 181% yield), as a off-white solid. The product was carried forward in the next step without further purification. MS (ESI) m/z 152.1 (MH+).

Workup

  1. customTo a nitrogen-purged round bottomed flask
  2. customHydrogen gas was bubbled through the solution for 1 minute
  3. customthe balloon was removed
  4. customthe round bottomed flask sealed with a rubber septum
  5. waitAfter 16 hours
  6. filtrationthe reaction was filtered through CELITE®
  7. washthe cake was washed liberally with EtOAc
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c6551874043043538662cba7a3be0d45
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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