5-Fluorouracil → HCID 12812862, compound

HRID 1702787Notes

Reaction equation

HRID 1702787 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]=[C:9]=[O:10])=[CH:3][CH:2]=1.[F:11][C:12]1[C:13](=[O:19])[NH:14][C:15](=[O:18])[NH:16][CH:17]=1>>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]([N:16]2[CH:17]=[C:12]([F:11])[C:13](=[O:19])[NH:14][C:15]2=[O:18])=[O:10])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 33855-FluorouracilHCID 204582734-(Isocyanatomethyl)pyridine

Product 1

HCID 12812862HCID 12812862, compound

Procedure

To the above solution of 4-pyridylmethyl isocyanate was added 5-fluorouracil (2.60 g.) at 80° C. and stirred for 4 hours at the same temperature. The resultant mixture was evaporated in vacuo. The residue was washed with diethyl ether (3 times) and crystallized. The crystals were filtered and washed with a small amount of ethanol. To the washed crystals a small amount of pyridine was added, and the mixture was warmed to be dissolved and cooled to be recrystallized. The crystals were washed successively with ethyl acetate and diethyl ether to give 1-[N-(4-pyridylmethyl)carbamoyl]-5-fluorouracil (1.75 g.)

Workup

  1. customThe resultant mixture was evaporated in vacuo
  2. washThe residue was washed with diethyl ether (3 times)
  3. customcrystallized
  4. filtrationThe crystals were filtered
  5. washwashed with a small amount of ethanol
  6. additionTo the washed crystals a small amount of pyridine was added
  7. temperaturethe mixture was warmed
  8. dissolutionto be dissolved
  9. temperaturecooled
  10. customto be recrystallized
  11. washThe crystals were washed successively with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-f856788c31b34ea696eca4220a64e135
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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