5-Methylfurfural → 1,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

HRID 624557Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1.[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH3:48][C:49]1[O:53][C:52]([CH:54]=O)=[CH:51][CH:50]=1>CCO>[CH3:22][N:7]1[C:6]2=[C:5]3[N:4]([C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:11]2[C:10](=[O:19])[N:9]([CH3:20])[C:8]1=[O:21])[CH2:3][CH2:2][O:1][CH:54]3[C:52]1[O:53][C:49]([CH3:48])=[CH:50][CH:51]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-(2-Hydroxyethyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Int C) (244 mg, 0.815 mmol), bismuth triflate (50.9 mg, 0.082 mmol, 10 mol %) and EtOH (2.4 mL) were treated with 5-methylfuran-2-carbaldehyde (commercially available, 0.089 mL, 0.082 mmol). The mixture was heated to 100° C. for 10 min using microwave irradiation. A further portion of 5-methylfuran-2-carbaldehyde (25 μL) was added to the reaction mixture and heating continued at 100° C. for 5 min. A solid formed on cooling, which was collected by reduced pressure filtration and washed with EtOH followed by diethyl ether, affording the title compound.

Workup

custommicrowave irradiation
temperatureheating
customA solid formed
temperatureon cooling
filtrationwhich was collected by reduced pressure filtration
washwashed with EtOH

Sources & evidence

ORD record: ord-14fceae83eec4374a5041d0d93cbae5a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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