Water → ethyl 5-fluoro-6-[(Z)5-methylfurfurylideneaminooxy]-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate

HRID 485312Notes

Reaction equation

HRID 485312 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.C(N(CC)CC)C.O>N1C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9581529HCID 9581529, compoundHCID 12946261HCID 12946261, compound

Product 1

HCID 13318207ethyl 5-fluoro-6-[(Z)5-methylfurfurylideneaminooxy]-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylateYield 51.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 70 ml of pyridine were dissolved 18.3 g (70 mmol) of ethyl 5-fluoro-6-acetoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate and 13.1 g (105 mmol) of (E)-5-methylfurfuraldoxime (containing 13% of the Z form), and 7.07 g (70 mmol) of triethylamine was added to the solution, followed by stirring at room temperature for 15 hours. The reaction solution was poured into 500 ml of ice-cooled water, and crystals precipitated were collected by filtration and washed with water. The crystals were dried under reduced pressure (P2O5) and recrystallized from 170 ml of ethanol to give 11.8 g of ethyl 5-fluoro-6-[(E)-5-methylfurfurylideneaminooxy]-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate. m.p. 181°-182° C.

Workup

  1. additionwas added to the solution
  2. customprecipitated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. dry with materialThe crystals were dried under reduced pressure (P2O5)
  6. customrecrystallized from 170 ml of ethanol

Sources & evidence

ORD record
ord-2e2977b90a084a479edb562220cd7b07
Source dataset
uspto-grants-1985_08
Patent number
US04536504

Reaction notes

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