Cesium carbonate → HCID 90459555, compound

HRID 714796Notes

Reaction equation

HRID 714796 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[N:7]=[C:6]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 775312,4-DichloropyrimidineHCID 634876Binap, (A+-)-

Product 1

HCID 90459555HCID 90459555, compoundYield 15.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 2,4-dichloropyrimidine (2.6 g), pyrrolidin-2-one (1.0 g), cesium carbonate (11 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (370 mg) in toluene (10 mL) was added tris(dibenzylideneacetone)dipalladium(0) (540 mg), and the mixture was stirred in a microwave reactor at 110° C. for 1.5 hr. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (370 mg).

Workup

  1. customThe insoluble substance was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a8099a890a494188a32b79257a2968e8
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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