Hydrochloric Acid → HCID 57642860, compound

HRID 2112898Notes

Reaction equation

HRID 2112898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[NH:16][C:17](=[O:27])[N:18]3[CH2:23][CH2:24][C:25]#[N:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]#[C:37][CH3:38].Cl>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[N:16]([CH2:35][C:36]#[C:37][CH3:38])[C:17](=[O:27])[N:18]3[CH2:23][CH2:24][C:25]#[N:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 57642811HCID 57642811, compound

Product 1

HCID 57642860HCID 57642860, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-[9-(2-Cyano-ethyl)-8-oxo-8,9-dihydro-7H-purin-6-yl]piperazine-1-carboxylic acid t-butyl ester (623 mg) was dissolved in N,N-dimethylformamide (10 mL). Potassium carbonate (300 mg) and 1-bromo-2-butyne (0.18 mL) were then added to this solution. The reaction solution was stirred at room temperature for 19 hours, then water (20 mL) and 1 N hydrochloric acid (5 mL) were added. This was then twice extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated brine. The resulting organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (484 mg).

Workup

  1. extractionThis was then twice extracted with ethyl acetate
  2. washthe obtained organic layer was washed with water and saturated brine
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f3f7ec1a44044395845bae7505705790
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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