HCID 11723521, compound → HCID 10242939, compound

HRID 646667Notes

Reaction equation

HRID 646667 reaction equation
[NH2:1][C:2]1[C:3]([C:22]([NH2:24])=[O:23])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14]CC3C=CC=CC=3)[CH:9]=2)=[CH:6][N:7]=1>[Pd].C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:22]([NH2:24])=[O:23])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 11723521HCID 11723521, compound

Product 1

HCID 10242939HCID 10242939, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 25 mL recovery flask was added 3-amino-6-{3-[(phenylmethyl)oxy]phenyl}pyrazine-2-carboxamide (33 mg, 0.103 mmol) and ethyl acetate (10 mL). A catalytic amount of 10% Pd/C was added. The flask was sealed with a septum and fitted with an H2 balloon. The reaction mixture was stirred overnight at room temperature. The reaction mixture was passed through a Celite pad. The filtrate was concentrated to give 3-amino-6-(3-hydroxyphenyl)pyrazine-2-carboxamide (23 mg, 96% yield) as a yeloow powder. 1H NMR (400 MHz, d6-DMSO): δ 9.47 (s, 1H), 8.74 (s, 1H), 7.55-7.53 (m, 1H), 7.46 (m, 1H), 7.25-7.22 (t, 1H), 6.78-6.76 (m, 1H); MS (EI) for C11H10N4O2: 231 (MH+).

Workup

  1. customThe flask was sealed with a septum
  2. customfitted with an H2 balloon
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9e0e1f0d5357414ebca0b0b8665e9085
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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