Ammonium Chloride → 2-Chloro-4-phenylpyrimidine

HRID 2252625Notes

Reaction equation

HRID 2252625 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Br-].[C:10]1([Zn+])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 775312,4-DichloropyrimidineHCID 178419759HCID 178419759, compound

Product 1

HCID 6053562-Chloro-4-phenylpyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis(triphenylphosphine)palladium (23 mg, 2 mol %) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at 50° C. for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried (MgSO4). Filtration and concentration of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine.

Workup

  1. extractionextracted with EtOAc twice
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration of solvent
  5. customgave a yellow residue which
  6. customwas purified by Prep

Sources & evidence

ORD record
ord-2313f8bb135946769576d5967a508542
Source dataset
uspto-grants-2008_01
Patent number
US07323447B2

Reaction notes

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