Sodium Carbonate → HCID 67286040, compound

HRID 1773050Notes

Reaction equation

HRID 1773050 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(#N)C>[CH3:9][C:10]1[CH:11]=[C:12]([C:2]2[CH:7]=[C:6]([C:14]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:9])[CH:15]=3)[N:5]=[CH:4][N:3]=2)[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 709434,6-DichloropyrimidineHCID 27339503-Tolylboronic acid2×

Product 1

HCID 67286040HCID 67286040, compoundYield 15%

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

First, into a recovery flask equipped with a reflux pipe were put 4.99 g of 4,6-dichloropyrimidine, 9.23 g of 3-methylphenylboronic acid, 7.18 g of sodium carbonate, 0.29 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile, 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. Here, into the flask were further put 2.31 g of 3-methylphenylboronic acid, 1.82 g of sodium carbonate, 0.070 g of Pd(PPh3)2Cl2, 5 mL of water, and 5 mL of acetonitrile, and the mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline, and was dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane and ethyl acetate as a developing solvent in a ratio of 20:1, so that a pyrimidine derivative H5mdppm, which was the objective substance, was obtained (pale yellow powder, yield of 15%). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme (d-1) of Step 1 is shown below.

Workup

  1. customFirst, into 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. temperaturethe mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes
  5. extractionan organic layer was extracted with dichloromethane
  6. washThe obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline
  7. dry with materialwas dried with magnesium sulfate
  8. customThe solution which had been dried
  9. filtrationwas filtered
  10. distillationThe solvent of this solution was distilled off
  11. customthe obtained residue was purified by silica gel column chromatography
  12. customwas obtained (pale yellow powder, yield of 15%)
  13. customNote that the irradiation with microwaves
  14. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  15. customA synthesis scheme (d-1) of Step 1

Sources & evidence

ORD record
ord-f66de2bc998a456aaf816285448920f0
Source dataset
uspto-grants-2016_02
Patent number
US09252380B2

Reaction notes

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