5,7-Dichloro-6-(2-fluorophenyl)-imidazo[1,2-a]pyrimidine → 7-Chloro-6-(2-fluorophenyl)-imidazo[1,2-a]pyrimidine

HRID 1851153Notes

Reaction equation

HRID 1851153 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18]>CO.C1COCC1.[Zn].[Cu]>[Cl:11][C:4]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:2][N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=1

Participants

5

Reactant 1

HCID 862136385,7-Dichloro-6-(2-fluorophenyl)-imidazo[1,2-a]pyrimidine

Product 1

HCID 867030217-Chloro-6-(2-fluorophenyl)-imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 3

HCID 10290809Zinc copper coupleCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.86 g (3.05 mmol) 5,7-Dichloro-6-(2-fluorophenyl)-imidazo[1,2-a]pyrimidine are given in 1.5 mL methanol and 8.6 mL THF. After addition of 0.589 g (4.6 mmol) zinc/copper pair the mixture is stirred at rt for 18 hours. The reaction mixture is filtered via a glass microfibre filter and washed with plenty of methanol. The solvent is evaporated and the residue is treated and evaporated three times with toluene. After chromatography on silicagel (eluents dichloromethane/methanol) 672.4 mg (89%) of the desired product containing bisdeschloro compound are obtained which is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered via a glass microfibre
  2. filtrationfilter
  3. washwashed with plenty of methanol
  4. customThe solvent is evaporated
  5. additionthe residue is treated
  6. customevaporated three times with toluene
  7. additionAfter chromatography on silicagel (eluents dichloromethane/methanol) 672.4 mg (89%) of the desired product containing bisdeschloro compound
  8. customare obtained which
  9. customis used without further purification

Sources & evidence

ORD record
ord-b163a4f7327e4663b21343c0487ed35a
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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