Water → 4-Chloro-6-(4-chlorophenyl)pyrimidine

HRID 271405Notes

Reaction equation

HRID 271405 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.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:8][C:6]1[CH:7]=[C:2]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:3]=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 742994-Chlorophenylboronic acid

Product 1

HCID 249020894-Chloro-6-(4-chlorophenyl)pyrimidineYield 58.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4,6-dichloropyrimidine (1.49 g, 10.0 mmol), 4-chlorophenylboronic acid (1.72 g, 11.0 mmol) and tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol) in toluene (20 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 10 mL, 20 mmol). The resulting reaction mixture was stirred at 100° C. under argon for 6 h, after which time analysis by HPLC/MS indicated that the reaction was complete. After cooling the reaction mixture to room temperature, water (50 mL) was added. The resulting mixture was extracted with EtOAc (50 mL). The organic layer was washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by trituration with MeOH (15 mL) to obtain 1.31 g of the title compound as a white solid (purity was about 80% by HPLC analysis). HPLC/MS: retention time=3.65 min, [M+H]30 =225.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by trituration with MeOH (15 mL)

Sources & evidence

ORD record
ord-5fae9e32d82046199a74abb086d9ce31
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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