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Theophylline → Diethyl [4-(1,3-dimethylxanthin-7-yl)butyl]phosphonate

HRID 1985
Notes
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Reaction equation

HRID 1985 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].Cl[CH2:15][CH2:16][CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][P:19](=[O:23])([O:24][CH2:25][CH3:26])[O:20][CH2:21][CH3:22])[CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 19689195Diethyl(4-chlorobutyl)phosphonate

Product 1

HCID 22446301Diethyl [4-(1,3-dimethylxanthin-7-yl)butyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

10.9 g (0.05 mol) of 1,3-dimethylxanthine were suspended in 150 ml of DMF, treated with 13.7 g (0.06 mol) of diethyl 4-chlorobutanephosphonate and 7.0 g (0.05 mol) of activated potassium carbonate and heated at 70° C. for approximately 4 hours. The solid was then filtered off, the filtrate was concentrated under reduced pressure and the oily residue which remained was taken up in ethyl acetate, filtered again and crystallized from diisopropyl ether.

Workup

  1. filtrationThe solid was then filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationfiltered again
  4. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-126b62e8f9c14b19bd96ee46b744d0b7
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728686

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes