Potassium Carbonate → 4-[7-(2-Butynyl)-1-(2-hydroxyethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1792011Notes

Reaction equation

HRID 1792011 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([CH2:23][C:24]#[C:25][CH3:26])[C:21]3[C:20](=[O:27])[NH:19][C:18](=[O:28])[N:17]([CH3:29])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][O:39]C1CCCCO1>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]([CH2:23][C:24]#[C:25][CH3:26])[C:21]3[C:20](=[O:27])[N:19]([CH2:37][CH2:38][OH:39])[C:18](=[O:28])[N:17]([CH3:29])[C:16]=3[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 230818994-[3-Methyl-7-(2-butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 235369394-[7-(2-Butynyl)-1-(2-hydroxyethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[3-Methyl-7-(2-butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.30 g) and potassium carbonate (0.21 g) were dissolved in N,N-dimethylformamide (10 ml), and 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.23 ml) was added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. After removing the solvent by distillation, ethanol (10 ml) and pyridinium p-toluenesulfonate (60 mg) were added to the resulting residue, and the reaction mixture was stirred at 60° C. for 3 hours. The reaction solution was distilled. The residue was purified by silica gel column chromatography to obtain 0.14 g of the title compound from a fraction eluted with hexane-ethyl acetate (1:5).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby distillation, ethanol (10 ml) and pyridinium p-toluenesulfonate (60 mg)
  5. additionwere added to the resulting residue
  6. stirringthe reaction mixture was stirred at 60° C. for 3 hours
  7. distillationThe reaction solution was distilled
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-114b8ffc9eab403194a1dff7ee465f7f
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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