Sodium Carbonate → 4,6-diphenylpyrimidine

HRID 534813Notes

Reaction equation

HRID 534813 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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>[C:9]1([C:2]2[CH:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 709434,6-Dichloropyrimidine

Product 1

HCID 8175404,6-diphenylpyrimidineYield 38%

Reagents, catalysts & solvents 4

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

Procedure

First, in a recovery flask equipped with a reflux pipe were put 5.02 g of 4,6-dichloropyrimidine, 8.29 g of phenylboronic acid, 7.19 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 one hour to be heated. Here, in the flask were further put 2.08 g of phenylboronic acid, 1.79 g of sodium carbonate, 0.070 g of Pd(PPh3)2Cl2, 5 mL of water, and 5 mL of acetonitrile, and the mixed solution was subjected to irradiation with microwaves (2.45 GHz, 100 W) for one hour to be heated. After that, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained extract was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. As a result, a pyrimidine derivative Hdppm (yellow white powder, yield of 38%) was obtained. Note that for the microwave irradiation, a microwave synthesis system (Discovery, produced by CEM Corporation) was used. A synthesis scheme (B-1) of Step 1 is shown below.

Workup

  1. customFirst, 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 one hour
  3. temperatureto be heated
  4. customthe mixed solution was subjected to irradiation with microwaves (2.45 GHz, 100 W) for one hour
  5. temperatureto be heated
  6. extractionan organic layer was extracted with dichloromethane
  7. extractionThe obtained extract
  8. washwas washed with water
  9. dry with materialdried with magnesium sulfate
  10. filtrationAfter the drying, the solution was filtrated
  11. distillationThe solvent of this solution was distilled off
  12. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6216059506643699ee5004822f2c569
Source dataset
uspto-grants-2014_10
Patent number
US08853724B2

Reaction notes

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