Sodium Carbonate → HCID 57584405, compound

HRID 1410397Notes

Reaction equation

HRID 1410397 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1B(O)O.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:11]2[CH:10]=[CH:9][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[N:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 709434,6-DichloropyrimidineHCID 2734375(Naphthalen-2-yl)boronic acid2×

Product 1

HCID 57584405HCID 57584405, compoundYield 48%

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 5.0 g of 4,6-dichloropyrimidine, 11.7 g of 2-naphthaleneboronic acid, 7.2 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 2.9 g of 2-naphthaleneboronic acid, 1.8 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 water and 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 hexane and ethyl acetate as a developing solvent in a ratio of 5:1, so that a pyrimidine derivative 4-chloro-6-(naphthalen-2-yl)pyrimidine, which was the objective substance, was obtained (yellow white powder, yield of 48%). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme (h-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 water
  6. dry with materialdried 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 (yellow white powder, yield of 48%)
  12. customNote that the irradiation with microwaves
  13. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  14. customA synthesis scheme (h-1) of Step 1

Sources & evidence

ORD record
ord-1e76c03883e847caa11d08ea06648a3a
Source dataset
uspto-grants-2014_12
Patent number
US08921548B2

Reaction notes

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