benzyl {5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-yl}carbamate → 5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-amine

HRID 2192923Notes

Reaction equation

HRID 2192923 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][C:13]([NH:16]C(=O)OCC2C=CC=CC=2)=[N:14][CH:15]=1>CO.C1COCC1.[C].[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=1

Participants

5

Reactant 1

HCID 59570908benzyl {5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-yl}carbamate

Product 1

HCID 595708905-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-amineYield 117.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl {5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-yl}carbamate (416 mg) in methanol (20 mL) and THF (10 mL) was added 10% palladium carbon (100 mg), followed by stirring for 2 hours under a hydrogen atmosphere. It was filtered through Celite and concentrated to obtain 5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-amine (305 mg) as a pale yellow oily substance.

Workup

  1. filtrationIt was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ae95b00a150040e6a911a6daee1d0d8a
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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