Ammonium Chloride → 2-Chloro-4-phenylpyrimidine

HRID 270677

Reaction equation

HRID 270677 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). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine to carry on.

Workup

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

Sources & evidence

ORD record
ord-ae6a541148514f6aaeb34a02b8f95f81
Source dataset
uspto-grants-2008_11
Patent number
US07449479B2

Linked notes

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