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

HRID 2189069Notes

Reaction equation

HRID 2189069 reaction equation
Cl/[C:2](/[N+]([O-])=O)=[CH:3]\[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][CH:5]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[N:19]=[CH:18][N:17]=1.N12CCCN=C1CCCCC2>C(O)C>[CH2:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]2[C:21]3[C:20](=[O:22])[NH:19][CH:18]=[N:17][C:16]=3[O:15][CH:2]=2)=[CH:5][CH:6]=1)[CH3:11]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 582802541-[(Z)-2-Chloro-2-nitrovinyl]-4-ethylbenzeneHCID 178516651HCID 178516651, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to the literature method [D. Dauzonne, Tetrahedron, 1992, 3069-3080], stir a suspension of 11.9 g (85% purity, 47.6 mmol) of 1-[(Z)-2-chloro-2-nitrovinyl]-4-ethylbenzene and 5.9 g (52.3 mmol) of 4,6-dihydroxypyrimidine in 200 ml of ethanol at 60-70° C. for 30 minutes. Then slowly add 14.4 ml (14.6 g, 96.1 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. Stir the resulting reaction solution under reflux for six hours and then at 60° C. for 15 hours. After concentration under reduced pressure, take up the residue in dichloromethane and chromatograph it on silica gel (eluent: cyclohexane/ethyl acetate 1:1→1:5). Stir the resulting solid in diethyl ether and filter. 5.0 g (44% of theory) of the target compound are obtained.

Workup

  1. stirringStir
  2. customthe resulting reaction solution
  3. temperatureunder reflux for six hours
  4. concentrationAfter concentration under reduced pressure
  5. stirringStir the resulting solid in diethyl ether
  6. filtrationfilter
  7. custom5.0 g (44% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-a33d35fc3b6e4601992846e4578e8a34
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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