Acetonitrile → 6-iodo-5-phenyl-3H-furo[2,3-d]pyrimidin-4-one

HRID 502634Notes

Reaction equation

HRID 502634 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][CH:12]=[N:11][C:10]=3[O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC#N.C1C(=O)N([I:27])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>ClC(Cl)C.CCOC(C)=O.O>[I:27][C:8]1[O:9][C:10]2[N:11]=[CH:12][NH:13][C:14](=[O:16])[C:15]=2[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 120273N-IodosuccinimideHCID 594278305-phenylfuro[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 586032796-iodo-5-phenyl-3H-furo[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 10 (1.0 g, 4.7 mmol) was dissolved in dichloroethane (50 mL) and CH3CN (50 mL) and NIS (1.7 g, 7.1 mmol) was added. The flask was equipped with a reflux condenser and the mixture was heated at reflux for 24 h. After cooling to RT and concentration, the crude reaction mixture was taken up in EtOAc and water. K2CO3 was added to raise the pH of the aqueous phase. After removal of the organic phase, the aqueous phase was extracted several times with EtOAc. The organics were then dried over Na2SO4 and concentrated to a brown oil. Flash chromatography (SiO2, gradient eluent: 25% EtOAc/Hexanes to 100% EtOAc) afforded 11.

Workup

  1. customThe flask was equipped with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 24 h
  4. concentrationconcentration
  5. customthe crude reaction mixture
  6. temperatureto raise the pH of the aqueous phase
  7. customAfter removal of the organic phase
  8. extractionthe aqueous phase was extracted several times with EtOAc
  9. dry with materialThe organics were then dried over Na2SO4
  10. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-f0b19515ee7d49f1adf93a59f0a57fd1
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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