Sodium Carbonate → HCID 15477739, compound

HRID 381277Notes

Reaction equation

HRID 381277 reaction equation
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31][C:32]1[N:37]=[C:36](Cl)[C:35]([Cl:39])=[CH:34][N:33]=1.[Cl:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][C:46]=1[Cl:47].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOCC.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.CCO>[Cl:31][C:32]1[N:37]=[C:36]([C:44]2[CH:43]=[CH:42][C:41]([Cl:40])=[C:46]([Cl:47])[CH:45]=2)[C:35]([Cl:39])=[CH:34][N:33]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 821241,4-Bis(diphenylphosphino)butaneHCID 2372592,4,5-TrichloropyrimidineHCID 27343303,4-Dichlorobenzeneboronic acid

Product 1

HCID 15477739HCID 15477739, compound

Reagents, catalysts & solvents 4

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 0.19 g (0.5 mmol) of bis(benzonitril)dichloro-palladium (II) and 0.2 g 1,4-bis(di-phenylphosphino)butane in 10 mL of toluene was heated at reflux with stirring for 1 h under nitrogen. The suspension was cooled to room temperature. One gram (6.6 mmol) of 3A, 1.57 g of 3,4-dichlorobenzene boronic acid (8.2 mmol), 2.5 mL EtOH and 5 mL of 1 M Na2CO3 were added and the mixture heated to reflux for 20 h. The reaction mixture was cooled and diluted with 100 mL Et2O. The suspension was filtered through a plug of silica gel and the cake washed with an additional 100 mL of Et2O. The ether was evaporated and the residue chromatographed over silica gel (10% EtOAc/hexane). A fraction containing 0.72 g (32%) of 2,5-dichloro-4-(3,4-dichlorophenyl)pyrimidine was isolated as a white solid. (m.p. 125-126° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture heated
  4. temperatureto reflux for 20 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationThe suspension was filtered through a plug of silica gel
  7. washthe cake washed with an additional 100 mL of Et2O
  8. customThe ether was evaporated
  9. customthe residue chromatographed over silica gel (10% EtOAc/hexane)
  10. additionA fraction containing 0.72 g (32%) of 2,5-dichloro-4-(3,4-dichlorophenyl)pyrimidine
  11. customwas isolated as a white solid

Sources & evidence

ORD record
ord-d9ba7e62842645c0a476620d9089f541
Source dataset
uspto-grants-2001_10
Patent number
US06306866B1

Reaction notes

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