Pyridine → HCID 57625978, compound

HRID 546557Notes

Reaction equation

HRID 546557 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.N1C=CC=CC=1.[C:34](Cl)(=[O:42])[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1.C(OCC)(=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:34](=[O:42])[O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:7]=3)[C:10]2=[O:27])=[CH:22][CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 57625970HCID 57625970, compound

Product 1

HCID 57625978HCID 57625978, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg of 1-[(2-aminopyrimidin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage f) of Example 1, in 3 mL of tetrahydrofuran, are added, at 0° C., 0.034 mL of pyridine and 0.045 mL of phenyl chlorocarbonate. The reaction mixture is stirred for 4.5 hours at room temperature and then diluted with ethyl acetate and washed with twice 30 mL of aqueous 1N hydrochloric acid solution, then with twice 30 mL of water, with twice 30 mL of saturated aqueous sodium hydrogen carbonate solution and finally with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with an ethyl acetate/cyclohexane mixture (62/38 by volume) to give 70 mg of phenyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]methyl}pyrimidin-2-yl)carbamate in the form of a white powder, the characteristics of which are as follows:

Workup

  1. washwashed with twice 30 mL of aqueous 1N hydrochloric acid solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluting with an ethyl acetate/cyclohexane mixture (62/38 by volume)

Sources & evidence

ORD record
ord-a94406d791d641918dd16dcabdb7e692
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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