Sodium Cyanide → HCID 23070605, compound

HRID 501415Notes

Reaction equation

HRID 501415 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])[C:10](Cl)=[N:9][C:8]=2[N:7]=[C:6]1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)[C:2]#[C:3][CH3:4].[C-:38]#[N:39].[Na+]>CN(C)C=O>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])[C:10]([C:38]#[N:39])=[N:9][C:8]=2[N:7]=[C:6]1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 23070724HCID 23070724, compound

Product 1

HCID 23070605HCID 23070605, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 8 mg of t-butyl 4-[7-(2-butynyl)-2-chloro-1-(2-cyanobenzyl)-6-oxo-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate obtained in Example 96(a), 10 mg of sodium cyanide and 0.3 ml of N,N-dimethylformamide was stirred at room temperature for 4 hours. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and then with saturated brine. The organic layer was concentrated. The residue was purified by thin layer chromatography (50% ethyl acetate/hexane) to give 6.1 mg of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate-water
  2. washthe organic layer was washed with water
  3. concentrationThe organic layer was concentrated
  4. customThe residue was purified by thin layer chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eb0931afd8be40ca87b088ffd5346618
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

Loading…