Acetic Acid → 4-Amino-2-phenyl-8-(2-deoxy-beta-D-ribofuranosyl)-pteridine-7-one

HRID 976935Notes

Reaction equation

HRID 976935 reaction equation
[Na].[NH2:2][C:3]1[C:12]2[N:11]=[CH:10][C:9](=[O:13])[N:8]([C@@H:14]3[O:28][C@H:27]([CH2:29][O:30]C(=O)C4C=CC(Cl)=CC=4)[C@@H:16]([O:17]C(=O)C4C=CC(Cl)=CC=4)[CH2:15]3)[C:7]=2[N:6]=[C:5]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:4]=1.CC(O)=O>CO>[NH2:2][C:3]1[C:12]2[N:11]=[CH:10][C:9](=[O:13])[N:8]([C@@H:14]3[O:28][C@H:27]([CH2:29][OH:30])[C@@H:16]([OH:17])[CH2:15]3)[C:7]=2[N:6]=[C:5]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 154039094-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-beta-D-ribofuranosyl]-pteridine-7-one

Product 1

HCID 154039144-Amino-2-phenyl-8-(2-deoxy-beta-D-ribofuranosyl)-pteridine-7-oneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10 mg of sodium in 50 mL of anhydrous methanol was added 0.632 g (1 mmol) of 4-amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorophenyl)-βD-ribofuranosyl]pteridine-7-one (4). The solution was stirred at room temperature for 1 hour. The solution was then neutralized by the addition of AcOH and then evaporated. The residue was recrystallized from methanol / H2O to give 5 as 0.323 g (91% yield) of colorless crystals (m.p. 169°-172° C.).

Workup

  1. customevaporated
  2. customThe residue was recrystallized from methanol / H2O

Sources & evidence

ORD record
ord-d7deae704e1748e4a0e52400fda3f2c7
Source dataset
uspto-grants-1997_03
Patent number
US05612468

Reaction notes

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