Triethylamine → HCID 13520569, compound

HRID 485311Notes

Reaction equation

HRID 485311 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.C(N(CC)CC)C>N1C=CC=CC=1>[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

5

Reactant 3

HCID 8471TriethylamineHCID 68712882-Furancarboxaldehyde, oximeHCID 13584398HCID 13584398, compound

Product 1

HCID 13520569HCID 13520569, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of pyridine were dissolved 2.9 g (10 mmol) of isobutyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 2.22 g (20 mmol) of (E)-furfuraldoxime, and 1.01 g (10 mmol) of dried triethylamine was added to the solution, followed by stirring at room temperature for 21 hours. The reaction solution was concentrated under reduced pressure, and 50 ml of ethyl acetate was added to the residue. The organic layer was washed three times with 10-ml portions of water, and the solvent was dried and evaporated under reduced pressure. The residue was recrystallized twice from ethyl acetate-hexane to give 2.39 g of isobutyl 5-fluoro-6-(E)-furfurylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate. m.p. 167°-168° C.

Workup

  1. additionwas added to the solution
  2. concentrationThe reaction solution was concentrated under reduced pressure, and 50 ml of ethyl acetate
  3. additionwas added to the residue
  4. washThe organic layer was washed three times with 10-ml portions of water
  5. customthe solvent was dried
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized twice from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ac82e42460784254bbc0ea3493e81ed8
Source dataset
uspto-grants-1985_08
Patent number
US04536504

Reaction notes

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