Cesium carbonate → 4-Chloro-6-phenylpyrimidine
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+]>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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
First, into a recovery flask equipped with a reflux pipe were put 3.35 g of 4,6-dichloropyrimidine, 3.02 g of phenylboronic acid, 1.7 mL of tricyclohexylphosphine (abbreviation: Cy3P), 14.7 g of cesium carbonate, 0.31 g of tris(dibenzylideneacetone)palladium(0) (abbreviation: Pd2(dba)3), and 30 mL of dioxane, and the air in the flask was replaced with argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes for reaction. The solvent of this 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). A synthesis scheme of Step 1 is shown in (b-1) given below.
Workup
- customFirst, into a recovery flask equipped with a reflux pipe
- temperatureThis reaction container was heated by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes for reaction
- distillationThe solvent of this solution was distilled off
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f97594e447ff494cbe8da9c08f9cb656
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09252380B2
Reaction notes
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