Pyridine → HCID 88632727, compound

HRID 1031432Notes

Reaction equation

HRID 1031432 reaction equation
N1C=CC=CC=1.[C:7]([CH:15]([OH:29])[C@H:16]1[O:20][C@@H:19]([N:21]2[CH:28]=[CH:27][C:25](=O)[NH:24][C:22]2=[O:23])[CH2:18][CH2:17]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:31]>O>[C:7]([CH:15]([OH:29])[C@H:16]1[O:20][C@@H:19]([N:21]2[CH:28]=[CH:27][C:25](=[S:31])[NH:24][C:22]2=[O:23])[CH2:18][CH2:17]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 70373655HCID 70373655, compound

Product 1

HCID 88632727HCID 88632727, compoundYield 157.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 50 ml of pyridine were dissolved 3.16 g of 5'-benzoyl-2',3'-dideoxy-uridine and 0.22 g of distilled water. Then, after added 2.67 g of phosphorus pentasulfide at room temperature under stirring, the mixture was refluxed for 3 hours. After the completion of reaction, the solids deposited by allowing to cool were collected by filtration, which were washed with small amount of pyridine. The pyridine filtrate obtained was concentrated to dryness and the residue was extracted with chloroform to separate 3.15 g of 5'-benzoyl-2',3'-dideoxy-4-thio-uridine(yield: 95%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customAfter the completion of reaction
  3. temperatureto cool
  4. filtrationwere collected by filtration, which
  5. washwere washed with small amount of pyridine
  6. customThe pyridine filtrate obtained
  7. concentrationwas concentrated to dryness
  8. extractionthe residue was extracted with chloroform

Sources & evidence

ORD record
ord-0b86a4bb0c78478e9869a02f01bef9ff
Source dataset
uspto-grants-1990_09
Patent number
US04954485

Reaction notes

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