Ammonia → 2-Iodoadenosine

HRID 1031855Notes

Reaction equation

HRID 1031855 reaction equation
Cl[C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19]C(=O)C)[C@H:13]1[O:14]C(=O)C.[NH3:30]>CO>[I:11][C:9]1[N:10]=[C:2]([NH2:30])[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=1)[C@@H:12]1[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([OH:19])[C@H:13]1[OH:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Product 1

HCID 1696622-IodoadenosineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.0 g of 6-chloro-2-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) purine was added to 60 ml of methanol plus ammonia (saturated at 0° C.) to cause reaction at a temperature of 60° C. for 17 hours in a sealed tube. The reaction solution was cooled, then degassed, and concentrated under reduced pressure. Crystallization of the residue from water afforded 3.94 g of 2-iodoadenosine (90% yield) having a melting point of 141° C. to 144° C.

Workup

  1. customreaction at a temperature of 60° C. for 17 hours in a sealed tube
  2. temperatureThe reaction solution was cooled
  3. customdegassed
  4. concentrationconcentrated under reduced pressure
  5. customCrystallization of the residue from water

Sources & evidence

ORD record
ord-95ea30a86ae94998a995aaccf8d84aeb
Source dataset
uspto-grants-1990_09
Patent number
US04956345

Reaction notes

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