Toluene → HCID 86709915, compound

HRID 1482171Notes

Reaction equation

HRID 1482171 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH:14]1[C:22]2[C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[S:19][C:18]=2[C:17]([C:27]2[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35](B(O)O)[CH:34]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(O)C>[CH:14]1[C:22]2[C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[S:19][C:18]=2[C:17]([C:27]2[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:2]4[CH:7]=[C:6]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[N:5]=[CH:4][N:3]=4)[CH:34]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5934294-Chloro-6-phenylpyrimidineHCID 58409996HCID 58409996, compound

Product 1

HCID 86709915HCID 86709915, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Then, 1.0 g of 4-chloro-6-phenylpyrimidine obtained in Step 1, 2.0 g of 3′-(dibenzothiophen-4-yl)-3-biphenylboronic acid, 5.3 mL of a 2M aqueous solution of potassium carbonate, 24 mL of toluene, and 3.0 mL of ethanol were put into a 100-mL three-neck flask equipped with a reflux pipe. Degasification by stirring under a reduced pressure was performed and the air in the flask was replaced with nitrogen. To this mixture, 61 mg of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added and the mixture was heated at 80° C. for 7 hours to cause a reaction. An organic layer was extracted from the obtained mixture with the use of toluene and was washed with water and a saturated aqueous solution of sodium chloride. Anhydrous magnesium sulfate was added and gravity filtration was performed. After the solvent in this solution was distilled off, the obtained residue was dissolved in hot toluene and subjected to hot filtration through a filter aid in which Celite, alumina, Celite, Florisil, and Celite were stacked in this order. The solvent was distilled off and the obtained solid was recrystallized with toluene, so that 1.9 g of a white solid was obtained in a yield of 71%. Synthesis Scheme (D-2) of Step 2 is shown below.

Workup

  1. customequipped with a reflux pipe
  2. customDegasification
  3. additionTo this mixture, 61 mg of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added
  4. customa reaction
  5. extractionAn organic layer was extracted from the obtained mixture with the use of toluene
  6. washwas washed with water
  7. additionAnhydrous magnesium sulfate was added
  8. filtrationgravity filtration
  9. distillationAfter the solvent in this solution was distilled off
  10. dissolutionthe obtained residue was dissolved in hot toluene
  11. filtrationsubjected to hot filtration through a filter aid in which Celite, alumina, Celite, Florisil, and Celite
  12. distillationThe solvent was distilled off
  13. customthe obtained solid was recrystallized with toluene, so that 1.9 g of a white solid
  14. customwas obtained in a yield of 71%
  15. customSynthesis Scheme (D-2) of Step 2

Sources & evidence

ORD record
ord-1ae1dc667e1346cb9737a2c4c13fa273
Source dataset
uspto-grants-2016_08
Patent number
US09412953B2

Reaction notes

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