HCID 67535989, compound → HCID 59301434, compound

HRID 2236190Notes

Reaction equation

HRID 2236190 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[N:15][C:14]([N:17]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[CH:13][N:12]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[CH3:22][O:21][CH2:20][CH2:19][N:17]([CH3:18])[C:14]1[CH:13]=[N:12][C:11]([NH2:10])=[CH:16][N:15]=1

Participants

5

Reactant 1

HCID 67535989HCID 67535989, compound

Product 1

HCID 59301434HCID 59301434, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above carbamic acid benzyl ester (316 mg, 1.0 mmol) was suspended in a mixture of methanol (25 mL) and THF (5 mL) containing 5% palladium on carbon (60 mg). The solution was placed under an atmosphere of hydrogen (hydrogen balloon) for one hour. The mixture was filtered through a thin layer of Celite and the solution was evaporated to give a green oil as N-(2-methoxyethyl)-N-methylpyrazine-2,5-diamine (180 mg, 100%). LCMS calcd for C8H14N4O (m/e) 182, obsd 183.1 (M+H).

Workup

  1. filtrationThe mixture was filtered through a thin layer of Celite
  2. customthe solution was evaporated

Sources & evidence

ORD record
ord-ff87d71bd635452b8bf9d05b0640245e
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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