Water → 7-Chloro-6-(4-fluorophenyl)-imidazo[1,2-a]pyrimidine

HRID 1851150Notes

Reaction equation

HRID 1851150 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][C:15]([F:18])=[CH:14][CH:13]=1.C1COCC1.O.[NH4+].[Cl-]>C(O)C.[Zn]>[Cl:11][C:4]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:2][N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 862136515,7-Dichloro-6-(4-fluorophenyl)-imidazo[1,2-a]pyrimidine

Product 1

HCID 867030197-Chloro-6-(4-fluorophenyl)-imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

5.3 g (18.9 mmol) 5,7-Dichloro-6-(4-fluorophenyl)-imidazo[1,2-a]pyrimidine are given in 480 mL ethanol, 184 mL THF and 342 mL water. After addition of 4.7 g (89.5 mmol) NH4Cl and 7.9 g (120 mmol) zinc the mixture is vigorously stirred at rt for two and a half hours. The reaction mixture is filtered via a glass microfibre filter and washed with plenty of methanol. The solvent has been removed and the residue redissolved in ethyl acetate (1 L). After washing twice with brine the solvent is evaporated (without prior drying due to solid material in the solvent). 3.83 g (81.8%) of the desired product containing 11% of the 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 has been removed
  5. dissolutionthe residue redissolved in ethyl acetate (1 L)
  6. washAfter washing twice with brine the solvent
  7. customis evaporated (
  8. customwithout prior drying due to solid material in the solvent)
  9. addition3.83 g (81.8%) of the desired product containing 11% of the bisdeschloro compound
  10. customare obtained which
  11. customis used without further purification

Sources & evidence

ORD record
ord-1ab23ea887d44b20a1347cd6aeb83fb6
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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