Ammonium Sulfate → 4-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-beta-D-ribofuranosyl]-pteridine-7-one

HRID 260143Notes

Reaction equation

HRID 260143 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8](=[O:12])[CH2:9][N:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[Cl:26][C:27]1[CH:52]=[CH:51][C:30]([C:31]([O:33][C@@H:34]2[C@@H:38]([CH2:39][O:40][C:41](=[O:49])[C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=3)[O:37][C@H:36](Cl)[CH2:35]2)=[O:32])=[CH:29][CH:28]=1>C[Si](C)(C)N[Si](C)(C)C.C(Cl)Cl.Cl([O-])(=O)(=O)=O.[Ag+]>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[N:7]([C@@H:36]3[O:37][C@H:38]([CH2:39][O:40][C:41](=[O:49])[C:42]4[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=4)[C@@H:34]([O:33][C:31](=[O:32])[C:30]4[CH:51]=[CH:52][C:27]([Cl:26])=[CH:28][CH:29]=4)[CH2:35]3)[C:6]=2[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

7

Reactant 3

HCID 6097028Ammonium SulfateHCID 9845541alpha-D-erythro-Pentofuranosyl chloride, 2-deoxy-, 3,5-bis(4-chlorobenzoate)HCID 544025114-Amino-2-phenyl-pteridine-7-one

Product 1

HCID 154039094-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-beta-D-ribofuranosyl]-pteridine-7-one

Reagents, catalysts & solvents 3

HCID 24562Silver perchlorateCatalystHCID 6344DichloromethaneSolventHCID 13838HexamethyldisilazaneSolvent2×

Procedure

A mixture of 1.0 g (4.2 mmol) of 4-amino-2-phenyl-pteridine-7-one (3) and a few crystals of ammonium sulfate was heated in 100 mL of hexamethyldisilazane (HMDS) under reflux for 4 hours. After cooling the excess HMDS was distilled off in vacuum and the residue dissolved in 100 mL of dry toluene. To the mixture was added 2.17 g (4.6 mmol) of 2-deoxy-3,5-di-O-(4-chlorobenzoyl)-α-D-ribofuranosyl chloride (made as in Example 3, step (a) for the toluyl derivative) and 0.476 g (2.3 mmol) of silver perchlorate. The solution was then stirred under anhydrous conditions for 24 hours at room temperature and then diluted with 200 mL of CH2Cl2. The resulting AgCl precipitate was filtered off through silica and then the flitrate was treated with 100 mL of a saturated aqueous solution of sodium bicarbonate followed by 100 mL of a saturated aqueous solution of NaCl. The organic layer was dried over Na2SO4, filtered and then the flitrate evaporated.

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationwas distilled off in vacuum
  3. dissolutionthe residue dissolved in 100 mL of dry toluene
  4. filtrationThe resulting AgCl precipitate was filtered off through silica
  5. additionthe flitrate was treated with 100 mL of a saturated aqueous solution of sodium bicarbonate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe flitrate evaporated

Sources & evidence

ORD record
ord-709d959ee68d47eb90ce4ec250c5f310
Source dataset
uspto-grants-1996_06
Patent number
US05525711

Reaction notes

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