HCID 54203965, compound → Theophylline

HRID 1732674Notes

Reaction equation

HRID 1732674 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]3C(=O)CCC[C:8]3=[N:7][C:6]=2[C:5](=[O:16])[N:4]([CH3:17])[C:3]1=[O:18]>CS(C)=O>[N:4]1([C:5](=[O:16])[C:6]2[NH:7][CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:18])[CH3:17]

Participants

3

Reactant 1

HCID 54203965HCID 54203965, compound

Product 1

HCID 2153TheophyllineYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.4 μmol flavin N6 -aminohexyl-adenine dinucleotide, prepared as described in part A of Example 1 above, in 200 μl dimethylsulfoxide under argon gas was added 0.9 mg 1,3-dimethyl-1,6,7,8-tetrahydropyrido[1,2-e]purine-2,4,9(3H)-trione (3.62 μmol), prepared according to the method of Cook et al, Res. Comm. in Chem. Pathol. and Pharm. 13:497 (1976), followed after 4 hours by addition of a further 1.8 mg (7.3 μmol) of the same. After stirring overnight, the solvent was evaporated under vacuum (0.1 mm Hg) and the residue chromatographed on a 2.5×90 cm LH-20 Sephadex (Pharmacia Fine Chemicals, Uppsala, Sweden) column and eluted with 0.3 M triethylammonium bicarbonate buffer (pH 7.8). The crude product eluted between 210 and 246 ml of the effluent, was collected, applied to a 20×20 cm×1000μ silica gel plate and eluted with an 8:2 ethanol: 1 M triethylammonium bicarbonate buffer (pH 7.8) mixture. The band containing the desired product (Rf =0.77) was scraped from the plate, extracted with 1 M triethylammonium bicarbonate buffer (pH 7.8), filtered and concentrated. Final purification by rechromatography on LH-20 Sephadex eluted with the buffer at 0.3 M gave 1.26 μmoles of the labeled conjugate, as determined by absorbance measurement at 450 nm, which was a yield of 53%.

Workup

  1. customprepared
  2. customprepared
  3. addition13:497 (1976), followed after 4 hours by addition of a further 1.8 mg (7.3 μmol) of the same
  4. customthe solvent was evaporated under vacuum (0.1 mm Hg)
  5. customthe residue chromatographed on a 2.5×90 cm LH-20 Sephadex (Pharmacia Fine Chemicals, Uppsala, Sweden) column
  6. washeluted with 0.3 M triethylammonium bicarbonate buffer (pH 7.8)
  7. washThe crude product eluted between 210 and 246 ml of the effluent,
  8. customwas collected
  9. washeluted with an 8:2 ethanol
  10. additionThe band containing the desired product (Rf =0.77)
  11. extractionextracted with 1 M triethylammonium bicarbonate buffer (pH 7.8)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customFinal purification by rechromatography on LH-20 Sephadex
  15. washeluted with the buffer at 0.3 M
  16. customgave 1.26 μmoles of the labeled conjugate

Sources & evidence

ORD record
ord-5ddf66c43ca741c49bfd164c77ad8981
Source dataset
uspto-grants-1980_12
Patent number
US04238565

Reaction notes

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