Methanol → HCID 86751192, compound

HRID 1376447Notes

Reaction equation

HRID 1376447 reaction equation
N[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2NC)=[C:4](CC)[N:3]=1.[F:15][C@@H:16]1[C@@H:20]([CH2:21][OH:22])[O:19][C@@H:18](N2C=CC(=O)NC2=O)[CH2:17]1.[N-]=[N+]=[N-].[K+].CO>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[F:15][C@@H:16]1[C@@H:20]([CH2:21][OH:22])[O:19][C@@H:18]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][CH:2]=[N:3][CH:4]=3)[CH2:17]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1624502',3'-Dideoxy-3'-fluorouridineHCID 10290740Potassium azideHCID 67703971HCID 67703971, compound

Product 1

HCID 86751192HCID 86751192, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Conditions

Temperature
45 °C

Procedure

2-Amino-6-ethylmethylamino-9H-purine (0.5 g, 2.6 mmoles) and 2',3'-dide-oxy-3'-fluorouridine (0.5 g, 2.2 mmoles) were suspended in potassium phosphate buffer (50 ml, 10 mM), pH 7.0, containing potassium azide 0.04%. Purine nucleoside phosphorylase (1120 I.U.) and thymidine phosphory-lase (10,000 I.U.) (Krenitsky et al., Biochemistry, 20, 3615 (1981) and U.S. Pat. No. 4,381,344) immobilized on DEAE cellulose was added to the reaction and the suspension was stirred at 45° C. After 7 days, MeOH (170 ml) was added to the reaction. The reaction was applied to a column containing AG1-X2 (OH- form, 2.5×10 cm) and eluted with MeOH. Fractions containing product were pooled, concentrated, and flash chromatographed on silica gel (2.5×20 cm) with dichloromethane:acetone (92:8). Product containing fractions were again pooled, concentrated, and flash chromatographed on silica gel (2.5×20 cm) with dichloromethane:meth-anol (95:5). Solvent was removed and lyophilization yielded 9-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofura-nosyl)-9H-purine (0.22 g, 32%): mp 89°-9° C.;

Workup

  1. additionwas added to the reaction
  2. additioncontaining AG1-X2 (OH- form, 2.5×10 cm)
  3. washeluted with MeOH
  4. additionFractions containing product
  5. concentrationconcentrated
  6. customflash chromatographed on silica gel (2.5×20 cm) with dichloromethane:acetone (92:8)
  7. additionProduct containing fractions
  8. concentrationconcentrated
  9. customflash chromatographed on silica gel (2.5×20 cm) with dichloromethane:meth-anol (95:5)
  10. customSolvent was removed

Sources & evidence

ORD record
ord-6cfa0fbfcacd4062a86d5b86c7530349
Source dataset
uspto-grants-1997_09
Patent number
US05663154

Reaction notes

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