HCID 5354160, compound → HCID 13520570, compound

HRID 485310Notes

Reaction equation

[F:1][C:2]1([C:14]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH:7]([O:8]C(=O)C)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13].[CH:21](=[N:27]/O)/[C:22]1[O:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.CC(C)=O>[F:1][C:2]1([C:14]([O:16][CH2:17][CH:18]([CH3:19])[CH3:20])=[O:15])[CH:7]([O:8]/[N:27]=[CH:21]\[C:22]2[O:26][CH:25]=[CH:24][CH:23]=2)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

In 45 ml of pyridine-acetone (pyridine:acetone=2:1) were dissolved 11.6 g (40 mmol) of isobutyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 6.1 g (54.9 mmol) of (Z)-furfuraldoxime, and the solution was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in 150 ml of ethyl acetate. The solution was washed three times with 50-ml portions of water, and the ethyl acetate layer was dried and the solvent was evaporated under reduced pressure. The residue was recrystallized three times from ethyl acetate-hexane to give 5.5 g of isobutyl 5-fluoro-6-(Z)-furfurylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate. m.p. 159°-160° C.

Workup

distillationThe solvent was distilled off under reduced pressure
dissolutionthe residue was dissolved in 150 ml of ethyl acetate
washThe solution was washed three times with 50-ml portions of water
dry with materialthe ethyl acetate layer was dried
customthe solvent was evaporated under reduced pressure
customThe residue was recrystallized three times from ethyl acetate-hexane

Sources & evidence

ORD record: ord-069d140b4fe64117a075828be4e2154c
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04536504

Reaction notes

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