Hydrazine → HCID 18660584, compound

HRID 343578Notes

Reaction equation

HRID 343578 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C@@H:10]2[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@H:11]2[N:18]2[CH:25]=[C:24]([CH3:26])[C:22](=[O:23])[NH:21][C:19]2=[S:20])C(=O)C2=CC=CC=C12.NN>CO>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C@@H:10]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[O:12][C@H:11]1[N:18]1[CH:25]=[C:24]([CH3:26])[C:22](=[O:23])[NH:21][C:19]1=[S:20]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 18660586Uridine, 2′-O-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-5-methyl-2-thio-

Product 1

HCID 18660584HCID 18660584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2'-O-Phthalimidopropyl-5-methyl-2-thiouridine (5.0 g, 15.8 mmol) is dissolved in 100 ml methanol in a 500 ml flask. Hydrazine (2.02 g, 63.2 mmol) is added and the mixture is heated to reflux (60°-65° C.) with stirring for 14 hours. The solvent is evaporated in vacuo and the residue is dissolved in dichloromethane (150 ml) and extracted twice with an equal volume NH4OH. The organic layer is evaporated to yield the crude product. NMR is used to assay product purity. The product is used in subsequent reactions without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux (60°-65° C.)
  3. customThe solvent is evaporated in vacuo
  4. dissolutionthe residue is dissolved in dichloromethane (150 ml)
  5. extractionextracted twice with an equal volume NH4OH
  6. customThe organic layer is evaporated

Sources & evidence

ORD record
ord-a64b4c31dd1548da97eb57ddd60c6d8e
Source dataset
uspto-grants-1999_01
Patent number
US05861493

Reaction notes

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