Theophylline → HCID 13041076, compound

HRID 1680637Notes

Reaction equation

HRID 1680637 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C([O-])([O-])=O.[K+].[K+].[C:20]([O:26][CH2:27]Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>CC(C)=O>[C:20]([O:26][CH2:27][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalate

Product 1

HCID 13041076HCID 13041076, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 3.60 g (0.02 mole) of theophylline and 1.38 g (0.01 mole) of K2CO3 in 75 ml of acetone was refluxed overnight and then allowed to react at reflux with 3.00 g (0.02 mole) of pivaloxymethyl chloride for 2 days. The suspension was filtered and the residue was washed with acetone (200 ml). The combined filtrate and wash was concentrated in vacuo and the residue was extracted with boiling heptane (200 ml). The heptane solution was cooled in the refrigerator for 0.5 hr then filtered. The residue was dried in vacuo to give 1.50 g (mp 108°-109.5°) of 7-pivaloxymethyl theophylline.

Workup

  1. temperaturewas refluxed overnight
  2. customto react
  3. filtrationThe suspension was filtered
  4. washthe residue was washed with acetone (200 ml)
  5. washThe combined filtrate and wash
  6. concentrationwas concentrated in vacuo
  7. extractionthe residue was extracted with boiling heptane (200 ml)
  8. temperatureThe heptane solution was cooled in the refrigerator for 0.5 hr
  9. filtrationthen filtered
  10. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-1f6bbd48b0f94e54917620756b2bdaa3
Source dataset
uspto-grants-1981_06
Patent number
US04275064

Reaction notes

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