Ethyl Acetate → HCID 135829586, compound

HRID 501374Notes

Reaction equation

HRID 501374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:15](=[O:17])[N:14](COC(=O)C(C)(C)C)[C:13](=[O:26])[NH:12][C:11]=2[N:10]=[C:9]1[N:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1.Br[CH:41]1[CH2:44][CH2:43][CH2:42]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13]([O:26][CH:41]3[CH2:44][CH2:43][CH2:42]3)=[N:12][C:11]=2[N:10]=[C:9]1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 23536936HCID 23536936, compound

Product 1

HCID 135829586HCID 135829586, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

8 mg of t-butyl 4-[7-(2-chlorophenyl)-1-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylate was dissolved in 0.3 ml of N,N-dimethylformamide, and 0.05 ml of bromocyclobutane and 20 mg of potassium carbonate were added thereto. The mixture was stirred at 50° C. overnight. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water. The organic layer was concentrated. The residue was dissolved in methanol, and 5 mg of sodium hydride was added to the solution. The mixture was stirred at room temperature for three hours. The reaction mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The solvent was concentrated, and the residue was dissolved in trifluoroacetic acid. The mixture was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid)) to give 1.89 mg of the title compound.

Workup

  1. washthe mixture was washed with water
  2. concentrationThe organic layer was concentrated
  3. dissolutionThe residue was dissolved in methanol
  4. addition5 mg of sodium hydride was added to the solution
  5. stirringThe mixture was stirred at room temperature for three hours
  6. extractionextracted with ethyl acetate
  7. concentrationThe solvent was concentrated
  8. dissolutionthe residue was dissolved in trifluoroacetic acid
  9. concentrationThe mixture was concentrated
  10. customthe residue was purified by reverse-phase high performance liquid chromatography (

Sources & evidence

ORD record
ord-e0b7fb4ed0c146838a47c52861effccb
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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