Carbon Tetrachloride → 5-Amino-1-(5-chloro-5-deoxy-beta-d-ribofuranosyl)imidazole-4-carboxamide

HRID 879953Notes

Reaction equation

HRID 879953 reaction equation
[CH:1]1[N:5]([C@@H:6]2[O:10][C@H:9]([CH2:11]O)[C@@H:8]([OH:13])[C@H:7]2[OH:14])[C:4]([NH2:15])=[C:3]([C:16]([NH2:18])=[O:17])[N:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.CO>[NH2:15][C:4]1[N:5]([C@@H:6]2[O:10][C@H:9]([CH2:11][Cl:39])[C@@H:8]([OH:13])[C@H:7]2[OH:14])[CH:1]=[N:2][C:3]=1[C:16]([NH2:18])=[O:17]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 17513Acadesine

Product 1

HCID 537964075-Amino-1-(5-chloro-5-deoxy-beta-d-ribofuranosyl)imidazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

AICA riboside (1.00 g), triphenylphosphine (3.05 g) and carbon tetrachloride (1.15 ml) were stirred in dimethyl formamide (38 ml) at room temperature for 3 hours. The solution was diluted with methanol (15 ml), then concentrated under reduced pressure. The resulting yellow tar was chromatographed on silica gel, eluting with 4:1 methylene chloride:methanol. The like fractions were combined and concentrated under reduced pressure to afford a purple foam. The presence of triphenylphosphine oxide, as determined by 1H NMR, necessitated a second chromotographic step as above. Yield was 0.43 g of a white foam.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting yellow tar was chromatographed on silica gel
  3. washeluting with 4:1 methylene chloride
  4. concentrationconcentrated under reduced pressure
  5. customto afford a purple foam

Sources & evidence

ORD record
ord-4e69ce4502574a80b09210e4e467c79f
Source dataset
uspto-grants-2015_03
Patent number
US08993527B2

Reaction notes

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