Tributylstannane → HCID 23536894, compound

HRID 1792077Notes

Reaction equation

HRID 1792077 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[CH:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[C:41]2[C:40](=[O:42])[N:39]([CH3:43])[C:38](=[O:44])[N:37]([CH3:45])[C:36]=2[N:35]=[CH:34]1)OC(SC)=S)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:10][CH:9]1[CH2:21][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[C:41]2[C:40](=[O:42])[N:39]([CH3:43])[C:38](=[O:44])[N:37]([CH3:45])[C:36]=2[N:35]=[CH:34]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86591949HCID 86591949, compound

Product 1

HCID 23536894HCID 23536894, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[1-[2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-phenyl]-1-methylsulfanylthiocarbonyloxymethyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (low polarity) (0.175 g), tributyltin hydride (0.25 g), and 2,2′-azobis(isobutyronitrile) (0.010 g) were dissolved in toluene (5 ml) under nitrogen atmosphere, and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled and the solvent was removed by distillation at reduced pressure. The residue was purified by silica gel column chromatography to give 0.123 g of the title compound from the elution fraction of hexane-ethyl acetate (1:1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed by distillation at reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-16033799dbbf4bf0af540394b12d32de
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

Loading…