Cesium carbonate → HCID 23630298, compound

HRID 546551Notes

Reaction equation

HRID 546551 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:10]2=[O:27])[CH:5]=[CH:4][N:3]=1.Br[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([N:11]2[C:12](=[O:16])[C:13]([CH3:15])([CH3:14])[N:9]([CH2:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[N:7]=3)[C:10]2=[O:27])=[CH:22][CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57625970HCID 57625970, compound

Product 1

HCID 23630298HCID 23630298, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a solution of 0.45 g of 1-[(2-aminopyrimidin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage f) in 15 mL of dioxane are successively added under argon 0.29 g of 3-bromopyridine, 1.51 g of caesium carbonate, 0.085 g of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 0.027 g of palladium acetate. The reaction medium is heated at 120° C. for 5 hours. After cooling, the reaction mixture is filtered, and the filtrate is concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica, eluting with dichloromethane, to give 76 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[2-(pyridin-3-ylamino)pyrimidin-4-ylmethyl]imidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by chromatography on a column of silica
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-93fcc110b54e4692bbb6b4d334e1810b
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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