5-Cyano-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester → 5-Aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

HRID 2076189Notes

Reaction equation

HRID 2076189 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([C:23]#[N:24])=[CH:7][N:6]=1)=[O:4]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:20])[CH3:21])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH2:24])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 591401375-Cyano-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 591401895-Aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-cyano-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester (600 mg, 1.74 mmol) in concentrated glacial acetic acid (12 mL) was added 10% Pd on carbon (120 mg). The reaction mixture was evacuated with vacuum and purged with H2 (3×), then stirred under an atmosphere of H2 for 3.5 hours. The reaction mixture was then filtered through a pad of Celite®. The filtrate was concentrated in vacuo to give the desired product as the HOAc salt. LCMS (method C): RT=2.51 min, [M+H]+=349.

Workup

  1. customThe reaction mixture was evacuated with vacuum
  2. custompurged with H2 (3×)
  3. filtrationThe reaction mixture was then filtered through a pad of Celite®
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e543e558d381479183c7ec499f0ceb30
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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