5-Fluorouracil → HCID 10688724, compound

HRID 615148Notes

Reaction equation

HRID 615148 reaction equation
[CH3:1][O:2][CH:3]1[CH:8]([O:9][CH3:10])[CH2:7][CH2:6][CH:5]([CH2:11][CH2:12][N:13]=[C:14]=[O:15])[CH2:4]1.[F:16][C:17]1[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=1>N1C=CC=CC=1>[CH3:1][O:2][CH:3]1[CH:8]([O:9][CH3:10])[CH2:7][CH2:6][CH:5]([CH2:11][CH2:12][NH:13][C:14]([N:21]2[CH:22]=[C:17]([F:16])[C:18](=[O:24])[NH:19][C:20]2=[O:23])=[O:15])[CH2:4]1

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 13364677HCID 13364677, compound

Product 1

HCID 10688724HCID 10688724, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.12 g of 2-(3, 4-dimethoxycyclohexyl) ethylisocyanate, 1.5 g of 5-fluorouracil and 50 ml of pyridine was heated at 90° C. for 2 hr. The solution was cooled to 50° C. and pyridine was evaporated under reduced pressure. The residue was shaked in a mixture of 80 ml of dichloromethane and 100 ml of hydrochloric acid water, and the lower layer of the solution was dried and evaporated. The residue was chromatographed on silica gel and 1.65 g of 1-(3, 4-dimethoxycyclohexylethylcarbamoyl)-5-fluorouracil (melting point: 129° C.) was obtained (Compound No. 8). NMR: 0.73-2.27 (9H b CH2) 2.77-3.40 (2H b CH2 --NH) 3.30-3.57 (H b CHOCH3) 3.35 (6H s OCH3) 3.50-3.77 (H b CHOCH3) 8.42 (H d C6 --H) 9.20 (H b NH CO).

Workup

  1. temperatureThe solution was cooled to 50° C.
  2. custompyridine was evaporated under reduced pressure
  3. additionThe residue was shaked in a mixture of 80 ml of dichloromethane and 100 ml of hydrochloric acid water
  4. customthe lower layer of the solution was dried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-64656d2c0dd34066bde6bd34d060be4d
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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