Potassium Carbonate → (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-pyridin-4-ylmethyl-amine

HRID 854443Notes

Reaction equation

HRID 854443 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>C(#N)C>[Br:1][C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 773174-PyridinemethanamineHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 58934041(6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-pyridin-4-ylmethyl-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6,8-Dibromo-imidazo[1,2-a]pyrazine 3 (1.0 equiv.), 4-aminomethylpyridine (1.0 equiv.) and potassium carbonate (3.0 equiv.) is dissolved in 20 ml 3:1 acetonitrile: dimethylacetamide and is stirred at 100° C. for 16 hours. The mixture is cooled to RT and partitioned between ethyl acetate (EtOAc) and saturated NaHCO3. The aqueous phase is extracted with EtOAc and combined extracts are dried over Na2SO4. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (EtOAc) to yield (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-pyridin-4-ylmethyl-amine 4.

Workup

  1. custompartitioned between ethyl acetate (EtOAc) and saturated NaHCO3
  2. extractionThe aqueous phase is extracted with EtOAc and combined extracts
  3. dry with materialare dried over Na2SO4
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting residue is purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-2f400c7cd74a4cf787769d1c5b4a6ca4
Source dataset
uspto-grants-2007_08
Patent number
US07259164B2

Reaction notes

Loading…