Cesium carbonate → HCID 66576563, compound

HRID 523599Notes

Reaction equation

HRID 523599 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)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].C1(C)C=CC=CC=1>[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH:1]3[CH2:3][CH2:2]3)[C:11]2=[O:15])[CH:22]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 709434,6-DichloropyrimidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576563HCID 66576563, compoundYield 18.18%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 11 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 500 mg, 2.46 mmol) was reacted with 4,6-dichloro-pyrimidine (403 mg, 2.70 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (117 mg, 0.246 mmol), Pd2(dba)3 (112 mg, 0.123 mmol), cesium carbonate (2.009 g, 6.15 mmol) and toluene (10 mL) in seal tube at 110° C. for 14 hours. Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 140 mg of the product (18.18% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-12049f60f151430c9d75c10577235263
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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