Iodine → 5-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

HRID 868503Notes

Reaction equation

HRID 868503 reaction equation
II.C(O[C@@H:7]1[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]1[O:9]C(=O)C)(=O)C.[NH:25]([C:32]1[CH:37]=[C:36]([Cl:38])[N:35]=[C:34]2[NH:39][CH:40]=[N:41][C:33]=12)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[NH:25]([C:32]1[CH:37]=[C:36]([Cl:38])[N:35]=[C:34]2[N:39]([C@@H:7]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]3[OH:9])[CH:40]=[N:41][C:33]=12)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 807IodineHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 178478243HCID 178478243, compound

Product 1

HCID 143917825-chloro-7-anilino-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridineYield 46.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
155 °C

Procedure

After a crystal of iodine was added to an intimate mixture of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5.2 g, 16 mMol) and 7-anilino-5-chloro-3H-imidazo[4,5-b]pyridine (4.0 g, 16 mMol), the mixture was heated in vacuo at 155° C. After 2 hours, the cooled reaction mixture was suspended in methanol and filtered to remove the unreacted heterocycle (2.29 g). The filtrate was taken to dryness in vacuo and treated with an excess of methanol previously saturated with ammonia. Purification by flash chromatography on silica gel (the residue was adsorbed onto silica gel and placed on the top of the column), elution with chloroform/methanol (20:1 v/v), and removal of the solvent gave 1.22 g (3.2 mMol) of 7-anilino-5-chloro-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine; yield 46.8%; m.p. 157°-160° C. UV max (nm) at pH 1, 307 (ε15,700); pH 13, 250 sh (ε9,900), 300 ε19,400); NMR (DMSO-d6): 9.42 d (s, 1H, NH); 8.50 (s, 1H, H2); 7.43-7.12 (m, 5H, Phenyl); 6.71 (s, 1H, H5); 5.93 (d, 1H, J=5.97 Hz, H1').

Workup

  1. customthe cooled reaction mixture
  2. filtrationfiltered
  3. customto remove the unreacted heterocycle (2.29 g)
  4. additiontreated with an excess of methanol previously saturated with ammonia
  5. customPurification by flash chromatography on silica gel (the residue
  6. washelution
  7. customwith chloroform/methanol (20:1 v/v), and removal of the solvent

Sources & evidence

ORD record
ord-403ae4446f244ecabba6954fbfa563c9
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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