Ethyl Acetate → HCID 23070800, compound

HRID 501376Notes

Reaction equation

HRID 501376 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](=[O:16])[NH:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)[C:2]#[C:3][CH3:4].Br[CH:31]([CH3:37])[C:32]([O:34]CC)=[O:33].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([O:16][CH:31]([C:32]([OH:34])=[O:33])[CH3:37])=[N:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 23070632HCID 23070632, compound

Product 1

HCID 23070800HCID 23070800, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

8 mg of t-butyl 4-[7-(2-butynyl)-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylate and 10 mg of ethyl 2-bromopropionate were dissolved in 0.2 ml of N,N-dimethylformamide, and 10 mg of potassium carbonate was added thereto. The mixture was stirred at 50° C. overnight. Ethyl acetate was added to the reaction solution, and the mixture was washed with water and 1N hydrochloric acid. The organic layer was concentrated to give t-butyl 4-[7-(2-butynyl)-2-(1-carboxyethoxy)-1-methyl-6-oxo-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate. This compound was dissolved in 0.4 ml of ethanol, and 0.1 ml of a 5N aqueous sodium hydroxide solution was added thereto. The mixture was stirred at room temperature for 3 hours. 1N-hydrochloric acid was added to the solution, and the mixture was extracted with ethyl acetate. The organic layer 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 3.37 mg of the title compound.

Workup

  1. washthe mixture was washed with water and 1N hydrochloric acid
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-fe53cdf3d4d44415b8e898db3e5e1f82
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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