Cesium carbonate → 1-(4-Cyclopropylpyridin-3-yl)-3-(2-methylpyrimidin-4-yl)imidazolidin-2-one

HRID 523608Notes

Reaction equation

HRID 523608 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[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[N:18]=1.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>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[N:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 4244474-Chloro-2-methylpyrimidineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 709845991-(4-Cyclopropylpyridin-3-yl)-3-(2-methylpyrimidin-4-yl)imidazolidin-2-oneYield 52.3%

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: 100 mg, 0.492 mmol) was reacted with 4-chloro-2-methylpyrimidine (68 mg, 0.541 mmol), 2-dicyclohexyl-phosphino-2′,4′,6′-triisopropylbiphenyl (23 mg, 0.0492 mmol), Pd2(dba)3 (23 mg, 0.024 mmol), cesium carbonate (400 mg, 1.23 mmol) and toluene (5 mL) in seal tube at 110° C. for 14 hours. Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 76 mg of the product (52% 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-eef9eba95a4a40c3944663670f60f0b3
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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