Potassium Phosphate, Tribasic → Methyl 3-amino-6-methylpyrazine-2-carboxylate

HRID 1093919Notes

Reaction equation

HRID 1093919 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].[CH3:13]OC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH3:13])[N:6]=1)=[O:4]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 58840780Methyl 3-amino-6-methylpyrazine-2-carboxylate

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester (1.0 g), palladium acetate (0.101 g), and S-Phos (2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl) were placed in a flask, with toluene (15 mL) and water (3 drops). Methyl boronic acid (0.394 g) and potassium phosphate (1.71 g) were added and the reaction mixture was refluxed for 24 hours. After allowing the reaction mixture to cool, the mixture was diluted with aqueous hydrochloric acid (1M) and extracted with ethyl acetate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent: diethyl ether) to give 3-amino-6-methylpyrazine-2-carboxylic acid methyl ester as a yellow solid (0.114 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (eluent: diethyl ether)

Sources & evidence

ORD record
ord-5461ce5797624bf3b2aa2a06dcf3e644
Source dataset
uspto-grants-2012_03
Patent number
US08133847B2

Reaction notes

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