Sodium Carbonate → 4,6-diphenylpyrimidine

HRID 2277573Notes

Reaction equation

HRID 2277573 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, into a recovery flask equipped with a reflux pipe, 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 were put, 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, into the flask, 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 were further put, and the reaction container was heated again by irradiation with microwaves (2.45 GHz, 100 W) for one hour. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained extract was washed with water, dried with magnesium sulfate, and then filtered. The solvent of the filtrate 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 the irradiation with microwaves was performed using a microwave synthesis system (Discover, produced by CEM Corporation). A synthesis scheme (a-1) of Step 1 is shown below.

Workup

  1. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for one hour
  2. temperatureto be heated
  3. temperaturethe reaction container was heated again by irradiation with microwaves (2.45 GHz, 100 W) for one hour
  4. extractionan organic layer was extracted with dichloromethane
  5. extractionThe obtained extract
  6. washwas washed with water
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. distillationThe solvent of the filtrate was distilled off
  10. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-666fe955a5f44c258f33fedfb274d305
Source dataset
uspto-grants-2015_09
Patent number
US09133169B2

Reaction notes

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