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

HRID 976934

Reaktionsgleichung

Reaktionsgleichung von HRID 976934
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24562Silver perchlorateKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 13838HexamethyldisilazaneLösungsmittel2×

Versuchsvorschrift

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 filtrate 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 filtrate evaporated.

Aufarbeitung

  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 filtrate 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 filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e1b73d28aa304de09ead78bae0f1502b
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612468

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