5-Fluorouracil → HCID 20525037, compound

HRID 1702792Notes

Reaction equation

HRID 1702792 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=1>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([N:20]1[CH:21]=[C:16]([F:15])[C:17](=[O:23])[NH:18][C:19]1=[O:22])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 33855-FluorouracilHCID 2052511776197-73-4

Product 1

HCID 20525037HCID 20525037, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To the above solution of 3-t-butoxycarbonylaminopropyl isocyanate was added a solution of 5-fluorouracil (2.60 g.) in N,N-dimethylacetamide (20 ml.) at 80° C. and stirred for further 3 hours at the same temperature. The resultant mixture was diluted with ethyl acetate (200 ml.), washed with water (each 30 ml., 3 times), dried over magnesium sulfate, treated with activated charcoal, filtered and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 1-[N-(3-t-butoxycarbonylaminopropyl)carbamoyl]-5-fluorouracil.

Workup

  1. washwashed with water (each 30 ml
  2. dry with material, 3 times), dried over magnesium sulfate
  3. additiontreated with activated charcoal
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4b15b764afa24eb0b26920d2dec96bd9
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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