Vinyl Acetate → 6-chloro-2-iodo-9-vinyl-9H-purine

HRID 2041927Notes

Reaction equation

HRID 2041927 reaction equation
C(O[CH:5]=[CH2:6])(=O)C.OS(O)(=O)=O.CCOC(C)=O.[I:18][C:19]1[N:27]=[C:26]2[C:22]([N:23]=[CH:24][NH:25]2)=[C:21]([Cl:28])[N:20]=1>[Hg](OC(C)=O)OC(C)=O>[Cl:28][C:21]1[N:20]=[C:19]([I:18])[N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][N:25]2[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 86628183Ethyl acetate sulfuric acidHCID 1784783676-Chloro-2-iodopurine

Product 1

HCID 577424006-chloro-2-iodo-9-vinyl-9H-purine

Reagents, catalysts & solvents 1

HCID 16683746DiacetyloxymercuryCatalyst

Conditions

Temperature
47.5 °C

Procedure

In a 250 mL pressure tube, Hg(OAc)2 (2.52 g, 7.88 mmol) was suspended in vinyl acetate (73 mL, 788 mmol). To this suspension was added H2SO4/EtOAc (1.5 mL/15 mL). A clear solution was formed. The 2-iodo-6-chloro-9H-purine (22.1 g, 78.8 mmol) was added. A suspension formed again. It was degassed and stirred at 45-50° C. overnight. A dark solution was formed. The mixture was passed through celite, washed with EtOAc. Organic layer was washed with Sat. NaHCO3, dried Na2SO4. The product was purified on silica gel chromatography column (1-5% MeOH/DCM).

Workup

  1. customA clear solution was formed
  2. customA suspension formed again
  3. customIt was degassed
  4. customA dark solution was formed
  5. washwashed with EtOAc
  6. washOrganic layer was washed with Sat. NaHCO3, dried Na2SO4
  7. customThe product was purified on silica gel chromatography column (1-5% MeOH/DCM)

Sources & evidence

ORD record
ord-9e44964519944fcebf6eb518dc8ff1c8
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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