Uracil → 5-Iodouracil

HRID 1055624Notes

Reaction equation

HRID 1055624 reaction equation
N1C=CC(=O)NC1=O.[I:9][C:10]1[C:11](=[O:21])[NH:12][C:13](=[O:20])[N:14](CC(O)=O)[CH:15]=1.C(C(N)CNCC(OCC)=O)(OC(C)(C)C)=O>>[I:9][C:10]1[C:11](=[O:21])[NH:12][C:13](=[O:20])[NH:14][CH:15]=1

Participants

4

Reactant 3

HCID 1174UracilHCID 1361763(5-Iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetic acidHCID 57253309HCID 57253309, compound

Product 1

HCID 696725-Iodouracil

Procedure

The PNA trimer can be synthesized manually or in an automated peptide synthesizer. The synthesis of universal base PNA monomer has been reported in the literature129,130 The modified uracil PNA monomer may be synthesized starting from 5-iodouracil-1-acetic acid.131 The starting material reacts with ethyl N-[2-Boc-aminoethyl]glycinate, providing a 5-iodouracil PNA monomer that can be converted into the desired product through the Sonogashira coupling132 with 3-benzoylthio-1-propyne followed by treating with di-tbutyl-1-(tbutylthio)hydrazine-1,2-dicarboxylate.34

Workup

  1. customThe synthesis of universal base PNA monomer
  2. custommay be synthesized

Sources & evidence

ORD record
ord-a69cfa82f3f64dcfbab481e5f1e4a4f6
Source dataset
uspto-grants-2016_07
Patent number
US09395352B2

Reaction notes

Loading…