Hydrochloric Acid → 1-(3-Hydroxy-3-methyl-4-pentynyl)-3-methyl-7-propylxanthine

HRID 1738792Notes

Reaction equation

HRID 1738792 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH3:13])[C:6]=2[C:5](=[O:14])[N:4]([CH2:15][CH2:16]C(=O)C)[C:3]1=[O:20].[C-:21]#[C-:22].[Li+].[Li+].[Cl-].[Ce+3].[Cl-].[Cl-].Cl.[O:30]1[CH2:35][CH2:34]OCC1>C1(C)C=CC=CC=1.O>[OH:30][C:35]([CH3:34])([C:21]#[CH:22])[CH2:16][CH2:15][N:4]1[C:5](=[O:14])[C:6]2[N:7]([CH2:11][CH2:12][CH3:13])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 312751,4-Dioxane2×HCID 153909233-Methyl-1-(3-oxobutyl)-7-propylxanthineHCID 178462446HCID 178462446, compound

Product 1

HCID 218393481-(3-Hydroxy-3-methyl-4-pentynyl)-3-methyl-7-propylxanthine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 55.7 g (0.2 mol) of 3-methyl-1-(3-oxobutyl)-7-propylxanthine in a mixture of 200 ml each of dioxane and toluene was added dropwise in 45 minutes to a stirred suspension of 36.8 g (0.4 mol) of lithium acetylide as ethylenediamine complex and 98.6 g (0.4 mol) of anhydrous cerium(III) chloride in a mixture of 500 ml each of dry dioxane and toluene at 50° C. The mixture was then stirred at 50° C. for 7 hours, cooled and, after addition of cold water and acidification with 2 N hydrochloric acid, intensively extracted with chloroform, the extract was washed with water, dried over sodium sulfate and evaporated under reduced pressure, and the residue was purified by filtration through a silica gel column in the eluent chloroform/methanol (50:1), resulting in 35.0 g (58% of theory) of solid, which was recrystallized from ethanol with large losses.

Workup

  1. temperaturecooled
  2. extractionintensively extracted with chloroform
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. filtrationthe residue was purified by filtration through a silica gel column in the eluent chloroform/methanol (50:1)
  7. customresulting in 35.0 g (58% of theory) of solid, which
  8. customwas recrystallized from ethanol with large losses

Sources & evidence

ORD record
ord-4b4f1570a05048a4987b41ef0679aeb2
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

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