5-Fluorouracil → 1-[N-(3-bromoadamantan-1-ylmethyl)carbamoyl]-5-fluorouracil

HRID 1702807Notes

Reaction equation

HRID 1702807 reaction equation
BrC12CC3CC(CC(CC(O)=O)(C3)C1)C2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Br:33][C:34]12[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][C:36]([CH2:44][N:45]=[C:46]=[O:47])([CH2:37]3)[CH2:35]1)[CH2:41]2.[F:48][C:49]1[C:50](=[O:56])[NH:51][C:52](=[O:55])[NH:53][CH:54]=1>N1C=CC=CC=1>[Br:33][C:34]12[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][C:36]([CH2:44][NH:45][C:46]([N:53]4[CH:54]=[C:49]([F:48])[C:50](=[O:56])[NH:51][C:52]4=[O:55])=[O:47])([CH2:37]3)[CH2:35]1)[CH2:41]2

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 199401P,P-Diphenylphosphinic azideHCID 27288372-(3-Bromoadamantan-1-yl)acetic acidHCID 205250663-Bromoadamantan-1-ylmethyl isocyanate

Product 1

HCID 205250721-[N-(3-bromoadamantan-1-ylmethyl)carbamoyl]-5-fluorouracil

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction of 3-bromoadamantan-1-ylacetic acid and diphenyl phosphoryl azide in dry pyridine provided a solution comprising 3-bromoadamantan-1-ylmethyl isocyanate [I.R.: 2270 cm-1 ], which was reacted with 5-fluorouracil to provide 1-[N-(3-bromoadamantan-1-ylmethyl)carbamoyl]-5-fluorouracil substantially by the similar method to that of Example 45.

Workup

  1. customprovided a solution

Sources & evidence

ORD record
ord-1caca980f0c44a7f8cc8aeebf5ffa6d4
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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