5-Fluorouracil → HCID 13216676, compound

HRID 615145Notes

Reaction equation

HRID 615145 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(Cl)=[O:11].[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][C:18]=1[O:25][CH3:26])[CH3:15].C(N(CC)CC)C>N1C=CC=CC=1>[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:10]([N:6]2[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]2=[O:8])=[O:11])=[CH:19][C:18]=1[O:25][CH3:26])[CH3:15]

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 6371PhosgeneHCID 8471TriethylamineHCID 71394601-(4-Ethoxy-3-methoxyphenyl)methanamine

Product 1

HCID 13216676HCID 13216676, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Fluorouracil, 1.14 g, was dissolved in 30 ml of pyridine, 2.46 g of phosgene was blown into the solution at 5° C., and the solution was allowed to stand at room temperature for 1 hr. Then 1.5 g of 4-ethoxy-3-methoxybenzylamine and 3.2 ml of triethylamine were added to it while cooling with ice, and the solution was stirred at room temperature for 1 hr. Triethylamine hydrochloride was removed from the solution by filtration. The filtrate was concentrated and exsiccated. The residue was dissolved in 100 ml of dichloromethane, and the solution was washed with hydrochloric acid water, dried, concentrated and exsiccated again. The residue was recrystallized from ethanol, and 2.3 g of 1-(4-ethoxy-3-methoxybenzylcarbamoyl)-5-fluorouracil (melting point: 153° C.) was obtained (Compound No. 5). NMR: (DMSOd6) 1.4-1.6 (3H, m, CH3) 3.85 (3H, s, OCH3) 4.04 (2H, q, OCH2) 4.44 (2H, d, CH2) 6.8 (2H, s, C6H2) 7.2 (1H, s, C6H) 8.42 (1H, d, H of the 6-position) 9.2 (1H, m, NH).

Workup

  1. customwas blown into the solution at 5° C.
  2. temperaturewhile cooling with ice
  3. customTriethylamine hydrochloride was removed from the solution by filtration
  4. concentrationThe filtrate was concentrated
  5. dissolutionThe residue was dissolved in 100 ml of dichloromethane
  6. washthe solution was washed with hydrochloric acid water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7ad3f4102d3a4e658603588cc9abe19a
Source dataset
uspto-grants-1985_02
Patent number
US04497815

Reaction notes

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