Cesium fluoride → 3-Methoxy-5-phenylpyrazin-2-amine

HRID 2217970Notes

Reaction equation

HRID 2217970 reaction equation
Br[C:2]1[N:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[F-].[Cs+].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:10][O:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 110308633-Methoxy-5-phenylpyrazin-2-amineYield 81.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

5-Bromo-3-methoxy-2-pyrazinamine (0.31 g), cesium fluoride (0.8 g), benzeneboronic acid (0.36 g) and [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) chloride (0.08 g) in methanol (7 mL) was heated at reflux for 2 hours. The solvent was evaporated and the residue purified by chromatography on silica eluting with toluene/ethyl acetate mixtures to give the sub-title compound (0.25 g).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue purified by chromatography on silica eluting with toluene/ethyl acetate

Sources & evidence

ORD record
ord-34439772743d4c6d956934e77180548d
Source dataset
uspto-grants-2008_08
Patent number
US07410972B2

Reaction notes

Loading…