Sodium Carbonate → HCID 67286040, compound

HRID 1410402Notes

Reaction equation

HRID 1410402 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+]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.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(#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 178418476HCID 178418476, compoundCatalystHCID 178419050HCID 178419050, 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 heated by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. 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. After that, 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 after drying 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 (n-1) of Step 1 is shown below.

Workup

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

Sources & evidence

ORD record
ord-aa8ccf08102240728fdfaf8657dcb58b
Source dataset
uspto-grants-2014_12
Patent number
US08921548B2

Reaction notes

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