Hydrochloric Acid → 1-(6-Dibutylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propyl-xanthine

HRID 1738793Notes

Reaction equation

HRID 1738793 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([N:10]([CH2:15][C:16]#C)[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9].[CH3:18][N:19]1[C:27]2[N:26]=[CH:25][N:24]([CH2:28][CH2:29][CH3:30])[C:23]=2[C:22](=[O:31])[N:21]([CH2:32][CH2:33][C:34](=[O:36])[CH3:35])[C:20]1=[O:37].Cl>CCCCCC.O1CCCC1>[CH2:11]([N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:15][C:16]#[C:35][C:34]([OH:36])([CH3:1])[CH2:33][CH2:32][N:21]1[C:22](=[O:31])[C:23]2[N:24]([CH2:28][CH2:29][CH3:30])[CH:25]=[N:26][C:27]=2[N:19]([CH3:18])[C:20]1=[O:37])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1387323-Dibutylamino-1-propyneHCID 153909233-Methyl-1-(3-oxobutyl)-7-propylxanthineHCID 178418339Butyllithium

Product 1

HCID 153909091-(6-Dibutylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propyl-xanthine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

6.73 ml (10.77 mmol) of a 15% strength butyllithium solution in n-hexane were slowly added dropwise to a solution of 2.09 ml (10.77 mmol) of N,N-dibutyl-2-propynylamine in 20 ml of tetrahydrofuran at -65° C. The mixture was stirred at -60° C. to -65° C. for one hour and warmed to room temperature, and a solution of 2.0 g (7.18 mmol) of 3-methyl-1-(3-oxobutyl)-7-propylxanthine in 30 ml of tetrahydrofuran was added. The slightly exothermic reaction was complete after 30 minutes. The mixture was adjusted to pH 5-6 with 1 N hydrochloric acid and partitioned between dichloromethane and water. The organic phase was washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The oily crude product was purified by flash chromatography, dichloromethane/methanol =19/0.75.

Workup

  1. customThe slightly exothermic reaction
  2. waitwas complete after 30 minutes
  3. custompartitioned between dichloromethane and water
  4. washThe organic phase was washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe oily crude product was purified by flash chromatography, dichloromethane/methanol =19/0.75

Sources & evidence

ORD record
ord-ab80205827d045e28210f06af697e415
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

Loading…