HCID 70103771, compound → HCID 70105569, compound

HRID 1288855Notes

Reaction equation

HRID 1288855 reaction equation
C(SC1N=C(SCCC)C2N=NN([C@@H:14]3[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C@@H:25]([O:26][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:15]3[O:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)C=2N=1)CC.[CH2:51]([S:54][C:55]1[N:56]=[C:57]([S:97][CH2:98][CH2:99][CH3:100])[C:58]2[C:59](=[N:61][N:62]([C@@H]3O[C@H](COC(=O)C4C=CC=CC=4)[C@@H](OC(=O)C4C=CC=CC=4)[C@H]3OC(=O)C3C=CC=CC=3)[N:63]=2)[N:60]=1)[CH2:52][CH3:53]>>[CH2:51]([S:54][C:55]1[N:56]=[C:57]([S:97][CH2:98][CH2:99][CH3:100])[C:58]2[N:63]([C@@H:14]3[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C@@H:25]([O:26][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:15]3[O:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:62]=[N:61][C:59]=2[N:60]=1)[CH2:52][CH3:53]

Participants

3

Reactant 2

HCID 70103771HCID 70103771, compoundHCID 70106863HCID 70106863, compound

Product 1

HCID 70105569HCID 70105569, compound

Procedure

Hydrogen bromide gas was bubbled into an ice-cooled solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2.02 g) in dichloromethane (15 ml) for 15 min. The reaction was stirred at 0° for 1 hour then at room temperature for 15 min. The solution was concentrated and the residue azeotroped with dichloromethane (3×50 ml). Sodium hydride (60%, 0.19 g) was added to a stirred suspension of the product of step b) (1.08 g) in acetonitrile (29 ml). After stirring at room temperature for 15 min the bromo sugar described above, in acetonitrile (10 ml), was added and stirring continued for 24 hours. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was dried and concentrated. Chromatography (SiO2, dichloromethane:diethylether, 39:1, as eluant) gave a mixture of 5,7-bis(propylthio)-3-(2,3,5-tri-O-benzoyl-β-D-ribo-furanosyl)-3H-1,2,3-triazolo[4,5-d]pyrimidine [MS (FAB): 714 (M+H+), 105 (100%)] and 5,7-bis(propylthio)-2-(2,3,5-tri-O-benzoyl-β-D-ribo-furanosyl)-2H-1,2,3-triazolo[4,5-d]pyrimidine [MS (FAB): 714 (M+H+), 105 (100%)] (1.9 g). Further elution gave 5,7-bis(propylthio)-1-(2,3,5-tri-O-benzoyl-β-D-ribo-furanosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine as a colourless foam (0.46 g).

Workup

  1. customHydrogen bromide gas was bubbled into an ice-
  2. temperaturecooled solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2.02 g) in dichloromethane (15 ml) for 15 min
  3. waitat room temperature for 15 min
  4. concentrationThe solution was concentrated
  5. customthe residue azeotroped with dichloromethane (3×50 ml)
  6. additionSodium hydride (60%, 0.19 g) was added to a stirred suspension of the product of step b) (1.08 g) in acetonitrile (29 ml)
  7. stirringAfter stirring at room temperature for 15 min the bromo sugar
  8. additionwas added
  9. stirringstirring
  10. waitcontinued for 24 hours
  11. customThe reaction mixture was partitioned between ethyl acetate and water
  12. customthe organic layer was dried
  13. concentrationconcentrated
  14. customChromatography (SiO2, dichloromethane:diethylether, 39:1, as eluant) gave
  15. washFurther elution

Sources & evidence

ORD record
ord-3ff4402f0c4a423092b251786fd0a335
Source dataset
uspto-grants-1998_05
Patent number
US05747496

Reaction notes

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