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

HRID 502633Notes

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

Conditions

Temperature: 60 °C

Procedure

The title compound 10 was prepared by the method of Dauzonne, D.; Adam-Launay, A. Tetrahedron 1992, 48, 3069-3080. 4,6-Dihydroxypyrimidine (3.3 g, 29.4 mmol) and (2-Chloro-2-nitro-vinyl)-benzene (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 4,6-Dihydroxypyrimidine. DBU (8.06 mL, 53.9 mmol) was then added drop-wise to the reaction. 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 crude 10 as an orange-red semisolid/oil. This material was triturated with 1.75:1 CH2Cl2/hexanes and solid 10 was isolated by Buchner filtration. Flash chromatography of the mother liquors afforded a second crop of solid 3 (>90% pure). The two crops were combined and concentrated to afford 10.

Workup

customThe title compound 10 was prepared by the method of Dauzonne, D
customto the reaction
temperaturewas heated
temperatureat reflux for 3 h
waitat 60° C. over night
temperatureThe deep red solution was then cooled to room temperature
concentrationconcentrated to a thick red oil
customPurification by flash chromatography (SiO2, gradient eluent: CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-6d943de371794a89b529e730c877f1bf
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776867B2

Reaction notes

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