Sodium Carbonate → HCID 117700666, compound

HRID 2275975Notes

Reaction equation

HRID 2275975 reaction equation
[C:1]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12]1([N:18]2[C:30]3[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]([C:5]1[CH:10]=[C:9]([C:27]2[CH:28]=[CH:29][C:30]3[N:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:19]4[C:24]([C:25]=3[CH:26]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 42892434-Chloro-6-(1,1-dimethylethyl)pyrimidineHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 117700666HCID 117700666, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Procedure

Next, in a recovery flask equipped with a reflux pipe were put 1.00 g of 4-tert-butyl-6-chloropyrimidine obtained in Step 2, 3.44 g of 9-phenyl-9H-carbazol-3-ylboronic acid, 1.32 g of sodium carbonate, 0.050 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: PdCl2(PPh3)2), 20 mL of water, and 20 mL of DMIF, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes to be heated. Then, water was added to this solution and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride, and was dried with magnesium sulfate. The solution obtained by the drying was filtered. The solvent of this solution was distilled off, and then the given residue was purified by flash column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 2:1 to give HtBupczpm (white powder, yield of 95%). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). Synthesis Scheme (a-3) of Step 3 is shown below.

Workup

  1. customNext, in a recovery flask equipped with a reflux pipe
  2. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes
  3. temperatureto be heated
  4. extractionthe organic layer was extracted with dichloromethane
  5. washThe obtained organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and was dried with magnesium sulfate
  7. customThe solution obtained by the drying
  8. filtrationwas filtered
  9. distillationThe solvent of this solution was distilled off
  10. customthe given residue was purified by flash column chromatography
  11. customto give HtBupczpm (white powder, yield of 95%)
  12. customNote that the irradiation with microwaves
  13. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  14. customSynthesis Scheme (a-3) of Step 3

Sources & evidence

ORD record
ord-75552ee8dc5f4ecb96df74e14d29268a
Source dataset
uspto-grants-2015_09
Patent number
US09130182B2

Reaction notes

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