5-Fluorouracil → 1-[N-(2-Adamantylmethyl)carbamoyl]-5-fluorouracil

HRID 1702808Notes

Reaction equation

HRID 1702808 reaction equation
C12CC3CC(CC(C3)C1CC(O)=O)C2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH:32]12[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[CH:33]1[CH2:42][N:43]=[C:44]=[O:45])[CH2:39]2.[F:46][C:47]1[C:48](=[O:54])[NH:49][C:50](=[O:53])[NH:51][CH:52]=1>N1C=CC=CC=1>[CH:34]12[CH2:40][CH:38]3[CH2:37][CH:36]([CH2:41][CH:32]([CH2:39]3)[CH:33]1[CH2:42][NH:43][C:44]([N:51]1[CH:52]=[C:47]([F:46])[C:48](=[O:54])[NH:49][C:50]1=[O:53])=[O:45])[CH2:35]2

Participants

6

Reactant 4

HCID 33855-FluorouracilHCID 199401P,P-Diphenylphosphinic azideHCID 8709902-(Adamantan-2-yl)acetic acidHCID 205250732-Adamantylmethyl isocyanate

Product 1

HCID 205250431-[N-(2-Adamantylmethyl)carbamoyl]-5-fluorouracil

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction of 2-adamantylacetic acid and diphenyl phosphoryl azide in dry pyridine provided a solution comprising 2-adamantylmethyl isocyanate [I.R.: 2260 cm-1 ], which was reacted with 5-fluorouracil to provide 1-[N-(2-adamantylmethyl)carbamoyl]-5-floururacil substantially in the similar method to that of Example 45.

Workup

  1. customprovided a solution
  2. customto provide 1-[N-(2-adamantylmethyl)carbamoyl]-5-floururacil substantially in the similar method to that of Example 45

Sources & evidence

ORD record
ord-866643fcacb14e62b407509b681ccefa
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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