Sodium Carbonate → 5-(4-Chlorophenyl)pyrazin-2-amine

HRID 1916732Notes

Reaction equation

HRID 1916732 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1>O1CCOCC1.CO>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 205670295-(4-Chlorophenyl)pyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere 50 mL 2 M Na2CO3 solution and 1.2 g (1.0 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 8.7 g (50.0 mmol) 5-bromo-pyrazin-2-ylamine and 8.0 g (50.0 mmol) 4-chlorophenyl-boric acid in 150 mL 1,4-dioxane and 50 mL MeOH and the reaction mixture is heated to 110° C. for 2.5 h. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: DCM to DCM/MeOH 20:1).

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted exhaustively with EtOAc
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis purified by chromatography (silica gel, gradient: DCM to DCM/MeOH 20:1)

Sources & evidence

ORD record
ord-d74b7ee5a66047f3bf8f9ef411294cb4
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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