Uridine → 9-beta-D-arabinofuranosyl-2-amino-6-iodo-9H-purine

HRID 21501

Reaction equation

HRID 21501 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([I:11])[N:3]=1.C1C(=O)NC(=O)N([C@@H:20]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@@H:21]2[OH:28])C=1.[N-]=[N+]=[N-].[K+].[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[C@@H:20]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH2:1])=[N:3][C:4]=3[I:11])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@@H:21]1[OH:28]

Participants

6

Reactant 4

HCID 6029Uridine2×HCID 18323Uracil ArabinosideHCID 61015752-Amino-6-iodopurineHCID 10290740Potassium azide

Product 1

HCID 538020069-beta-D-arabinofuranosyl-2-amino-6-iodo-9H-purineYield 11%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Conditions

Temperature
37 °C

Procedure

2-Amino-6-iodopurine (Sigma Chemicals, St. Louis. Mo.) (25.5 mmoles, 6.75 g) and uracil arabinoside (61.9 mmoles, 15.1 g) were combined in 0.31 liters of 10 mM potassium phosphate pH 6.9 with 0.02% potassium azide. Purified purine nucleoside phosphorylase (17000 units) and uridine phosphorylase (2000 units) were added and the solution stirred at 37° C. After 18 days an additional 5700 units of uridine phosphorylase were added. Fifty-seven days later the reaction was filtered and the filtrate chromatographed on a column containing XAD-2 resin (8×11 cm). The product was eluted with a step gradient of ethanol/water (v/v) as follows: 0.35 liter 10%; 1 liter 20%; 1 liter 50%; 0.2 liter 95%. Product-containing fractions were combined and the ethanol removed under vacuum. The residue was dissolved in 30% n-propanol/water (v/v) and chromatographed on a 7.5×90 cm column containing BioRad P-2 resin. This procedure yielded 1.1 g of 9-β-D-arabinofuranosyl-2-amino-6-iodo-9H-purine as a 0.5 hydrate. NMR and mass spectrometry were consistent with the structure. Anal. Calcd. for C10H12IN5O4.05H2O: Calcd: C, 29.87; H, 3.26; N, 17.41. Found: C, 29.86; H, 3.29; N, 17.39.

Workup

  1. filtrationFifty-seven days later the reaction was filtered
  2. customthe filtrate chromatographed on a column
  3. additioncontaining XAD-2 resin (8×11 cm)
  4. washThe product was eluted with a step gradient of ethanol/water (v/v)
  5. customthe ethanol removed under vacuum
  6. dissolutionThe residue was dissolved in 30% n-propanol/water (v/v)
  7. customchromatographed on a 7.5×90 cm column
  8. additioncontaining BioRad P-2 resin

Sources & evidence

ORD record
ord-e17b8b329b094e1dae974da8c7bcf4f4
Source dataset
uspto-grants-1995_06
Patent number
US05424295

Linked notes

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