Ethyl Bromide → HCID 20335668, compound

HRID 1706371Notes

Reaction equation

HRID 1706371 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[C:6]=2[C:5](=[O:17])[NH:4][C:3]1=[O:18].[OH-].[Na+].[CH2:21](Br)[CH3:22]>CO.O>[CH2:21]([N:4]1[C:5](=[O:17])[C:6]2[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:18])[CH3:22]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 13298152HCID 13298152, compound

Product 1

HCID 20335668HCID 20335668, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

20 g of 3-methyl-7-(hex-5-enyl)-xanthine (see Example 22) are added to a solution of approximately 3.3 g of NaOH in 70 ml of methanol/water (1:1) and 9 g of ethyl bromide are added thereto. The mixture is kept at 40° C. under a nitrogen atmosphere for 40 hours. The solvent is then removed under reduced pressure, the residue dissolved in diethyl ether and the pH of the solution is adjusted with aqueous sodium hydroxide solution to a pH-value of 13.5 to remove unreacted 3-methyl-7-(hex-5-enyl)-xanthine. 1-Ethyl-3-methyl-7-(hex-5-enyl)-xanthine recovered from the ether phase is subsequently subjected to column chromatography using silica gel with methylene chloride/acetone (8:2) as eluent followed by distillation under reduced pressure and is obtained as a colourless oil. Yield: 11.2 g (81.3% of theory relative to reacted starting material) of the title compound, nD20 =1.5415.

Workup

  1. additionare added
  2. customThe solvent is then removed under reduced pressure
  3. dissolutionthe residue dissolved in diethyl ether
  4. customto remove unreacted 3-methyl-7-(hex-5-enyl)-xanthine
  5. custom1-Ethyl-3-methyl-7-(hex-5-enyl)-xanthine recovered from the ether phase
  6. distillationfollowed by distillation under reduced pressure
  7. customis obtained as a colourless oil

Sources & evidence

ORD record
ord-6d3b893e43f448acbdc25f2c6027bb15
Source dataset
uspto-grants-1980_06
Patent number
US04207321

Reaction notes

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