Cesium carbonate → HCID 65647653, compound

HRID 1410403Notes

Reaction equation

HRID 1410403 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>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].O.O1CCOCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])[N:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 8188604,6-Dichloro-5-methylpyrimidineHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 65647653HCID 65647653, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

First, into a recovery flask equipped with a reflux pipe were put 5.0 g of 4,6-dichloro-5-methylpyrimidine, 4.6 g of 2-methylphenylboronic acid, 20 g of cesium carbonate, 2.5 mL of 15% toluene solution of tricyclohexylphosphine (abbreviation: Cy3P), 0.47 g of tris(dibenzylideneacetone)dipalladium (0) (abbreviation: Pd2(dba)3), and 40 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, 150 W) for 2 hours. After that, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline, and was 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 dichloromethane as a developing solvent and the obtained fraction was concentrated, so that 4-chloro-5-methyl-6-(2-methylphenyl)pyrimidine was obtained (a white solid, yield of 58%). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme (q-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, 150 W) for 2 hours
  3. extractionan organic layer was extracted with dichloromethane
  4. washThe obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline
  5. dry with materialwas dried with magnesium sulfate
  6. customThe solution after drying
  7. filtrationwas filtered
  8. distillationThe solvent of this solution was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography
  10. concentrationthe obtained fraction was concentrated, so that 4-chloro-5-methyl-6-(2-methylphenyl)pyrimidine
  11. customwas obtained (a white solid, yield of 58%)
  12. customNote that the irradiation with microwaves
  13. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  14. customA synthesis scheme (q-1) of Step 1

Sources & evidence

ORD record
ord-079d533e255b48b8bf2a4a3620043c19
Source dataset
uspto-grants-2014_12
Patent number
US08921548B2

Reaction notes

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