N-Iodosuccinimide → 5-(4-Ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one

HRID 2189070Notes

Reaction equation

HRID 2189070 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24](=[O:26])[NH:23][CH:22]=[N:21][C:20]=3[O:19][CH:18]=2)=[CH:13][CH:12]=1)[CH3:10]>C(#N)C.ClC(Cl)(Cl)Cl>[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:25]3[C:24](=[O:26])[NH:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[I:1])=[CH:15][CH:16]=1)[CH3:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 582801005-(4-Ethylphenyl)furo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 582801285-(4-Ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 18669661Acetonitrile tetrachloromethaneSolvent

Procedure

Add 7.0 g (31.3 mmol) of N-iodosuccinimide to a solution of 5.0 g (20.9 mmol) of 5-(4-ethylphenyl)furo[2,3-d]pyrimidin-4(3H)-one in 250 ml of acetonitrile/tetrachloromethane (1:1). Stir the resulting suspension under reflux for two hours. After cooling to room temperature, concentrate the reaction mixture under reduced pressure. Stir the residue in ethyl acetate and filter. Add water to the filtrate. After removal of the organic phase, extract the aqueous phase repeatedly with ethyl acetate. Concentrate the combined organic phases under reduced pressure. Take up the residue in ethyl acetate and chromatograph it on silica gel (eluent: cyclohexane/ethyl acetate 1:1→1:2). Stir the resulting solid in diethyl ether/n-pentane and filter. 1.4 g (85% purity, 16% of theory) of the target compound are obtained.

Workup

  1. temperatureunder reflux for two hours
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. stirringStir the residue in ethyl acetate
  4. filtrationfilter
  5. customAfter removal of the organic phase
  6. extractionextract the aqueous phase repeatedly with ethyl acetate
  7. concentrationConcentrate the combined organic phases under reduced pressure
  8. stirringStir the resulting solid in diethyl ether/n-pentane
  9. filtrationfilter
  10. custom1.4 g (85% purity, 16% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-85a78d902a304e239b90b5a591cb5f0a
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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