HCID 5399175, compound → HCID 13318208, compound

HRID 485309Notes

Reaction equation

HRID 485309 reaction equation
[F:1][C:2]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]([O:8]C(=O)C)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13].[CH3:19][C:20]1[O:27][C:23](/[CH:24]=[N:25]\O)=[CH:22][CH:21]=1>N1C=CC=CC=1.CC(C)=O>[F:1][C:2]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]([O:8]/[N:25]=[CH:24]\[C:23]2[O:27][C:20]([CH3:19])=[CH:21][CH:22]=2)[NH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13]

Participants

4

Reactant 2

HCID 5399175HCID 5399175, compoundHCID 12946261HCID 12946261, compound

Product 1

HCID 13318208HCID 13318208, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 21978327HCID 21978327, compoundSolvent

Procedure

In 75 ml of pyridine-acetone (pyridine:acetone=2:1) were dissolved 20 g (76 mmol) of ethyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 11.4 g (91 mol) of (Z)-5-methylfurfuraldoxime, and the solution was stirred at room temperature for 4 days. The reaction solution was concentrated under reduced pressure, and the residue was treated with water. Crystals precipitated were collected by filtration and washed with water. The crystals were dried under reduced pressure and dissolved in acetone, and insoluble matters were filtered off. The filtrate was concentrated, and the residue was chromatographed on silica gel with chloroform-acetone (7:1), followed by recrystallization from ethyl acetate-hexane to yield 4.6 g of ethyl 5-fluoro-6-[(Z)5-methylfurfurylideneaminooxy]-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate. m.p. 163°-164° C.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe residue was treated with water
  3. customCrystals precipitated
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customThe crystals were dried under reduced pressure
  7. dissolutiondissolved in acetone
  8. filtrationinsoluble matters were filtered off
  9. concentrationThe filtrate was concentrated
  10. customthe residue was chromatographed on silica gel with chloroform-acetone (7:1)
  11. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-27573d4aca264045b6caa6a922f0305c
Source dataset
uspto-grants-1985_08
Patent number
US04536504

Reaction notes

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