Tetrahydrofuran → HCID 57642811, compound

HRID 2112897Notes

Reaction equation

HRID 2112897 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N+:20]([O-])=O)=[C:18]([NH:23][CH2:24][CH2:25][C:26]#[N:27])[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:28]1CCC[CH2:29]1>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][N:17]=[C:18]3[C:19]=2[NH:20][C:29](=[O:28])[N:23]3[CH2:24][CH2:25][C:26]#[N:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57642848HCID 57642848, compound

Product 1

HCID 57642811HCID 57642811, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-[6-(2-Cyano-ethylamino)-5-nitro-pyrimidin-4-yl]piperazine-1-carboxylic acid t-butyl ester (1.0 g) was dissolved in tetrahydrofuran (12 mL), and then 10% palladium on carbon powder (wet type) (200 mg) was added to this solution. The reaction solution was stirred under a hydrogen atmosphere at room temperature for 20 hours. Insoluble substances were then removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was dissolved in acetonitrile (30 mL), and then N,N′-disuccinimidyl carbonate (1.13 g) was added to this solution. The reaction solution was stirred at room temperature for five hours, then 40 mL of water was added. This reaction solution was then concentrated under reduced pressure to 40 mL. The precipitate was collected by filtration. The obtained solid was washed with water and hexane to give the title compound (623 mg). A portion of the obtained compound was purified by silica gel column chromatography for use in NMR analysis.

Workup

  1. customInsoluble substances were then removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in acetonitrile (30 mL)
  4. additionN,N′-disuccinimidyl carbonate (1.13 g) was added to this solution
  5. stirringThe reaction solution was stirred at room temperature for five hours
  6. addition40 mL of water was added
  7. concentrationThis reaction solution was then concentrated under reduced pressure to 40 mL
  8. filtrationThe precipitate was collected by filtration
  9. washThe obtained solid was washed with water and hexane

Sources & evidence

ORD record
ord-c251ff8bd8e14bf7b41b93ad2c348009
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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