Water → 2,6-Diacetamido-9-(Triacetyl-beta-D-Ribofuranosyl)Purine

HRID 1730482Notes

Reaction equation

HRID 1730482 reaction equation
[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([NH:9][CH:10]=[N:11]2)=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[N:6]=1)(=[O:3])[CH3:2].O.[C:19]([C@@:22]1([OH:37])[C@@H:26]([CH2:27][OH:28])[O:25][C:24](Cl)([C:29](=[O:31])[CH3:30])[C@:23]1([C:34](=[O:36])[CH3:35])[OH:33])(=[O:21])[CH3:20]>C1(C)C(C)=CC=CC=1>[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@:24]2([C:29](=[O:31])[CH3:30])[O:25][C@H:26]([CH2:27][OH:28])[C@@:22]([C:19](=[O:21])[CH3:20])([OH:37])[C@@:23]2([C:34](=[O:36])[CH3:35])[OH:33])=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 13923314N,N'-(7H-Purine-2,6-diyl)diacetamideHCID 131710526triacetyl D-ribofuranosyl chloride

Product 1

HCID 1317105252,6-Diacetamido-9-(Triacetyl-beta-D-Ribofuranosyl)Purine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

The dried chloromercuri derivative (24 g., 0.05 mole) of 2,6-diacetamidopurine was refluxed in xylene using a Dean-Stark water separator. Freshly prepared triacetyl-D ribofuranosyl chloride in xylene was added to the hot chloromercuri derivative and the mixture was refluxed, in an oil bath, with vigorous stirring. After 41/2 hours the reaction mixture was allowed to stand overnight at room temperature and then filtered. The precipitate was extracted (several times) with warm CHCl3. The CHCl3 extract was washed successively with 30% aqueous KI (thrice), water (thrice) dried, charcoaled and filtered. The filtrate was evaporated in vacuo, and the residue on trituration with ether gave 14.3 g. (58%; m.p. 87°-92°) of 2,6-diacetamido-9-triacetyl-β-D-ribofuranosyl purine.

Workup

  1. temperaturethe mixture was refluxed, in an oil bath, with vigorous stirring
  2. custom2 hours
  3. filtrationfiltered
  4. extractionThe precipitate was extracted (several times) with warm CHCl3
  5. extractionThe CHCl3 extract
  6. washwas washed successively with 30% aqueous KI (thrice), water (thrice)
  7. customdried
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo
  10. customthe residue on trituration with ether gave 14.3 g

Sources & evidence

ORD record
ord-cbba8632b6944152ae88048f3909f606
Source dataset
uspto-grants-1976_11
Patent number
US03992531

Reaction notes

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