Cesium carbonate → 4-Chloro-6-phenylpyrimidine

HRID 1499031Notes

Reaction equation

HRID 1499031 reaction equation
[Cl:1][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.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 709434,6-DichloropyrimidineHCID 75806Tricyclohexylphosphine

Product 1

HCID 5934294-Chloro-6-phenylpyrimidineYield 34%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Into a recovery flask equipped with a reflux pipe, 3.35 g of 4,6-dichloropyrimidine, 3.02 g of phenylboronic acid, 1.7 mL of tricyclohexylphosphine (abbreviation: PCy3), 14.7 g of cesium carbonate, 0.31 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3), and 30 mL of dioxane were put, and the air in the flask was replaced by argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent of this reaction solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and hexane as a developing solvent in a volume ratio of 1:1, to give 4-chloro-6-phenylpyrimidine (light yellow powder, 34% in yield). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 1 is shown by (a-1).

Workup

  1. temperatureThis reaction container was heated by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes
  2. distillationThe solvent of this reaction solution was distilled off
  3. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e1d07fc80844c7e85e3452d141b1dee
Source dataset
uspto-grants-2015_12
Patent number
US09200022B2

Reaction notes

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