Benzene → 5-Propyl-2'-deoxyuridine

HRID 1679871

Reaction equation

HRID 1679871 reaction equation
[CH2:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)[CH2:2][CH3:3].C[Si](Cl)(C)C.C1C=CC=CC=1.ClC1C=CC(C([C@@:30]2([OH:47])[C@@H:34]([CH:35](C(=O)C3C=CC(Cl)=CC=3)[OH:36])[O:33][CH:32](Cl)[CH2:31]2)=O)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH2:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[N:8]([CH:9]=1)[C@@H:32]1[O:33][C@H:34]([CH2:35][OH:36])[C@@H:30]([OH:47])[CH2:31]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6397ChlorotrimethylsilaneHCID 732695-Propyluracil2×HCID 22816183HCID 22816183, compound

Product 1

HCID 1601555-Propyl-2'-deoxyuridineYield 166.5%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 15,4 g 5-propyluracil (0.1 mole) and 21,7 g trimethylsilyl chloride (0,2 mole) in 250 ml anhydrous benzene 20.2 g dry triethylamine (0,2 mole) are added dropwise under stirring and exclusion of humidity within a time span of 15 minutes. After further stirring for about 12 hours the unreacted 5-propyl-uracil and the precipitated dry ethylamine hydrochloride are separated and the filtrate is concentrated under vacuum. The residue is dissolved in 150 ml of absolute toluene and under stirring a solution of 43 g 3,5-di-(p-chlorobenzoyl)-2-desoxy-D-ribofuranosyl chloride (0,1 mole) in 500 ml toluene and thereafter 31,8 g mercury (II)-acetate are added and the stirring is continued another 24 hours. After filtration the filtrate is extracted with a 30% aqueous potassium iodide solution and thereafter washed with water. After drying over sodium sulfate the toluene solution is concentrated to approximately 100 ml. Upon standing the protected nucleoside crystallizes. 45 g of a product with melting point 140°-165° C. are obtained.

Workup

  1. customwithin a time span of 15 minutes
  2. customthe precipitated dry ethylamine hydrochloride are separated
  3. concentrationthe filtrate is concentrated under vacuum
  4. dissolutionThe residue is dissolved in 150 ml of absolute toluene
  5. filtrationAfter filtration the filtrate
  6. extractionis extracted with a 30% aqueous potassium iodide solution
  7. washwashed with water
  8. dry with materialAfter drying over sodium sulfate the toluene solution
  9. concentrationis concentrated to approximately 100 ml
  10. customcrystallizes

Sources & evidence

ORD record
ord-7f07142bd86f4d97b4ba043dbf53adaf
Source dataset
uspto-grants-1981_06
Patent number
US04271153

Linked notes

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