5-Fluorouracil → 1-[N-(1-adamantylmethyl)carbamoyl]-5-fluorouracil

HRID 1702774Notes

Reaction equation

HRID 1702774 reaction equation
[C:1]12([CH2:11][N:12]=[C:13]=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]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]12([CH2:11][NH:12][C:13]([N:20]3[CH:21]=[C:16]([F:15])[C:17](=[O:23])[NH:18][C:19]3=[O:22])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 2

HCID 33855-FluorouracilHCID 219066941-(Isocyanatomethyl)adamantane

Product 1

HCID 205250961-[N-(1-adamantylmethyl)carbamoyl]-5-fluorouracil

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To the above solution of 1-adamantylmethyl 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 diethyl ether to give 1-[N-(1-adamantylmethyl)carbamoyl]-5-fluorouracil (1.85 g), as colorless crystalline powder.

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 diethyl ether

Sources & evidence

ORD record
ord-56241a24c506499297b3126c554310f7
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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