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

HRID 1926900Notes

Reaction equation

HRID 1926900 reaction equation
Cl/[C:2](/[N+]([O-])=O)=[CH:3]\[C:4]1[CH:9]=[CH:8][C:7]([O: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>[CH3:11][O: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

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58207481-(2-Chloro-2-nitrovinyl)-4-methoxybenzeneHCID 178516651HCID 178516651, compound

Product 1

HCID 580169685-(4-Methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As in the procedure described in the literature [D. Dauzonne, Tetrahedron, 1992, 3069-3080], stir a suspension of 10.1 g (47.4 mmol) 1-[(Z)-2-chloro-2-nitrovinyl]-4-methoxybenzene and 5.8 g (52.2 mmol) 4,6-dihydroxypyrimidine in 200 ml ethanol for ten minutes at 85° C. Next, slowly add 15.6 ml (15.9 g, 104.3 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene. Stir for 15 h at this temperature and then concentrate by vacuum evaporation. Take up the residue in dichloromethane and chromatograph on silica gel (solvent: dichloromethane/methanol 95:5). Mix the solid obtained with acetonitrile and then filter. 2.3 g (20% of theor.) of the target product is obtained.

Workup

  1. stirringStir for 15 h at this temperature
  2. concentrationconcentrate by vacuum evaporation
  3. additionMix the solid
  4. customobtained with acetonitrile
  5. filtrationfilter
  6. custom2.3 g (20% of theor.) of the target product is obtained

Sources & evidence

ORD record
ord-d4caadb6a34b45a8a1b7485076442ae9
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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