Methanol → HCID 15005404, compound

HRID 1886176Notes

Reaction equation

HRID 1886176 reaction equation
[Na].[H][H].Cl[C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[C:8]([CH3:22])[N:9]2[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1.[CH3:23][OH:24]>>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([N:9]2[C:8]([CH3:22])=[N:7][C:6]3[C:10]2=[N:11][CH:12]=[N:13][C:5]=3[O:24][CH3:23])=[CH:15][CH:16]=1)#[N:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 15005410HCID 15005410, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15005404HCID 15005404, compoundYield 83%

Procedure

Sodium metal (160 mg, 6.96 mmol) was allowed to react with dry methanol (5 ml) under nitrogen until evolution of hydrogen had ceased. 6-Chloro-9-(4-cyanophenyl)-8-methylpurine (1.03 g, 3.82 mmol) was added in one portion and the resulting slurry was heated under reflux for 90 minutes. The solvent was removed under reduced pressure and the residual gum was dissolved in dichloromethane (50 ml). The solution was washed with brine (20 ml), dried (MgSO4) and concentrated under reduced pressure to give the title compound, (840 mg, 83%).

Workup

  1. temperaturethe resulting slurry was heated
  2. temperatureunder reflux for 90 minutes
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residual gum was dissolved in dichloromethane (50 ml)
  5. washThe solution was washed with brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11dcbfa4002a4c2ab9d9b53260ac5c9b
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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