Cesium carbonate → HCID 178440998, compound

HRID 546629Notes

Reaction equation

HRID 546629 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[N:33][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:28][C:29]4[CH:34]=[N:33][C:32]([OH:35])=[CH:31][CH:30]=4)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 576259713-(4-Tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)HCID 178507770HCID 178507770, compound

Product 1

HCID 178440998HCID 178440998, compoundYield 5.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.5 g of 3-(4-tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage a) of Example 7 in 15 mL of dioxane are successively added, under argon, 285 mg of 5-amino-2-hydroxypyridine, 1.6 g of caesium carbonate, 90 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) [xantphos] and 29 mg of palladium diacetate. The reaction mixture is heated at 100° C. for 1 hour, filtered and concentrated under reduced pressure. The residue is successively purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (95/5 by volume) followed by HPLC (gradient: water/acetonitrile containing 0.1% formic acid) to give 35 mg of 3-(4-tert-butylphenyl)-1-({2-[(6-hydroxypyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is successively purified by chromatography on a column of silica
  4. washeluting with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record
ord-8f523719e8d44afa9a05adf4078a6cb8
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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