5-Fluorouracil → HCID 10824012, compound

HRID 615149Notes

Reaction equation

HRID 615149 reaction equation
[CH:1]1([N:6]=[C:7]=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[C:11](=[O:17])[NH:12][C:13](=[O:16])[NH:14][CH:15]=1>N1C=CC=CC=1>[CH:1]1([NH:6][C:7]([N:14]2[CH:15]=[C:10]([F:9])[C:11](=[O:17])[NH:12][C:13]2=[O:16])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 643500Cyclopentyl Isocyanate

Product 1

HCID 10824012HCID 10824012, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopentylisocyanate, 5.67 g, was allowed to react with 5-fluorouracil, 4.6 g, in 17 g of pyridine at 90° C. for 2 hr, then the pyridine was evaporated and the residue was shaken with 100 ml of dichloromethane and 100 ml of hydrochloric acid water. The lower layer of the mixture was dried and exsiccated. The residue was recrystallized from ethanol and 8.3 g of 1-cyclopentylcarbamoyl-5-fluorouracil (melting point: 137° C.) was obtained (Compound No. 9) was obtained. NMR: 1.00-2.28 (6H b CH) 3.56-4.12 (1H b CH--NHCO) 8.40 (1H d C6 --H) 8.68-9.08 (1H b NHCO) 9.48 (1H b N3 --H).

Workup

  1. customthe pyridine was evaporated
  2. customThe lower layer of the mixture was dried
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-290e9480034b45848a787f625dcacead
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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