Diethyl Ether → A 802715

HRID 1602129Notes

Reaction equation

HRID 1602129 reaction equation
C[Mg]Cl.[CH3:4][N:5]1[C:13]2[N:12]=[CH:11][N:10]([CH2:14][CH2:15][CH3:16])[C:9]=2[C:8](=[O:17])[N:7]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[C:6]1=[O:25].[CH3:26]COCC.[Cl-].[NH4+]>O1CCCC1>[OH:24][C:22]([CH3:26])([CH3:23])[CH2:21][CH2:20][CH2:19][CH2:18][N:7]1[C:8](=[O:17])[C:9]2[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[N:12][C:13]=2[N:5]([CH3:4])[C:6]1=[O:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4938PropentofyllineHCID 25517Ammonium ChlorideHCID 178418332HCID 178418332, compound

Product 1

HCID 129959A 802715

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

22.4 g (0.3 mol) of methylmagnesium chloride in the form of a 20% strength solution in tetrahydrofuran are added dropwise with vigorous stirring at room temperature to a suspension of 61.3 g (0.2 mol) of 3-methyl-1-(5-oxohexyl)-7-propylxanthine in 2 1 of anhydrous ether, the internal temperature rising to approximately 30° C. The mixture is then warmed with stirring and under reflux for 2 hours, treated with saturated aqueous ammonium chloride solution to decompose the alkoxide formed, and the organic phase is separated off and washed twice with 500 ml of water each time. The collected water phases are extracted thoroughly with dichloromethane again. The dichloromethane extract is combined with the ethereal phase, dried over sodium sulfate, filtered and evaporated under reduced pressure, 59.0 g of crude product (91.5% of theory) being obtained, which is purified by recrystallization from diisopropyl ether.

Workup

  1. customrising to approximately 30° C
  2. temperatureThe mixture is then warmed
  3. temperatureunder reflux for 2 hours
  4. customformed
  5. customthe organic phase is separated off
  6. washwashed twice with 500 ml of water each time
  7. extractionThe collected water phases are extracted thoroughly with dichloromethane again
  8. extractionThe dichloromethane extract
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure, 59.0 g of crude product (91.5% of theory)
  12. custombeing obtained
  13. customwhich is purified by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-6ed7cf8995a548398f2f224903274b33
Source dataset
uspto-grants-1999_11
Patent number
US05981536

Reaction notes

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