1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-phenylfuro[2,3-d]pyrimidin-4(3H)-one

HRID 502661Notes

Reaction equation

HRID 502661 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[CH:4][N:3]=1.Cl[C:10]([N+]([O-])=O)=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CCN2C(=NCCC2)CC1>CCO>[C:12]1([C:11]2[C:7]3[C:6](=[O:8])[NH:5][CH:4]=[N:3][C:2]=3[O:1][CH:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 53695982(2-Chloro-2-nitrovinyl)benzeneHCID 178516651HCID 178516651, compound

Product 1

HCID 594278305-phenylfuro[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared by the method of Dauzonne, D.; Adam-Launay, A. Tetrahedron 1992, 48, 3069-3080. 4,6-Dihydroxypyrimidine 161 (3.3 g, 29.4 mmol) and 160 (5.3 g, 26.7 mmol) were combined in EtOH (absolute, 110 mL) and the mixture was heated at 60° C. for 10 min to dissolve 161. DBU (8.06 mL, 53.9 mmol) was then added drop-wise. After addition of DBU the deep green-brown solution was heated at reflux for 3 h then at 60° C. over night. The deep red solution was then cooled to room temperature and concentrated to a thick red oil. Purification by flash chromatography (SiO2, gradient eluent: CH2Cl2 to 5% MeOH/CH2Cl2) to afford as an orange-red semisolid/oil. This material was triturated with 1.75:1 CH2Cl2/hexanes and solid 162 was isolated by Buchner filtration (−95% pure). Flash chromatography of the mother liquors afforded a second crop of solid 162 (>90% pure). The two crops were combined and concentrated to afford 162 as a pale orange solid (69% yield).

Workup

  1. customThe title compound was prepared by the method of Dauzonne, D
  2. dissolutionto dissolve 161
  3. temperaturewas heated
  4. temperatureat reflux for 3 h
  5. waitat 60° C. over night
  6. temperatureThe deep red solution was then cooled to room temperature
  7. concentrationconcentrated to a thick red oil
  8. customPurification by flash chromatography (SiO2, gradient eluent: CH2Cl2 to 5% MeOH/CH2Cl2)
  9. customto afford as an orange-red semisolid/oil
  10. customThis material was triturated with 1.75:1 CH2Cl2/hexanes

Sources & evidence

ORD record
ord-895cbfa31bf34ae5af9485c12d55cf4a
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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