Homoallyl bromide → HCID 13298149, compound

HRID 1762553Notes

Reaction equation

HRID 1762553 reaction equation
[Na].[CH3:2][N:3]1[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[C:6](=[O:12])[NH:5][C:4]1=[O:13].Br[CH2:15][CH2:16][CH:17]=[CH2:18]>CN(C)C=O>[CH2:18]([N:8]1[C:7]2[C:6](=[O:12])[NH:5][C:4](=[O:13])[N:3]([CH3:2])[C:11]=2[N:10]=[CH:9]1)[CH2:17][CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 21241Homoallyl bromideHCID 706393-MethylxanthineHCID 5360545Sodium

Product 1

HCID 13298149HCID 13298149, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

47 g (0.25 mol) of the monosodium salt of 3-methylxanthine (prepared as described in Example 1b) and 34.8 g (0.25 mol) of 97% strength 1-bromo-3-butene in 750 ml of dimethylformamide are stirred for 8 hours at 110° C. Thereafter, the precipitated sodium bromide is removed by filtration of the still hot reaction mixture, the filtrate is concentrated in vacuo, the solid residue is dissolved in 250 ml of 2N sodium hydroxide solution, the solution is heated to about 65° C. and 2N hydrochloric acid is added, while stirring, until the pH reaches 9. After cooling, the solid formed is filtered off under suction, washed salt-free with water, rinsed with methanol and then dried in vacuo.

Workup

  1. customThereafter, the precipitated sodium bromide is removed by filtration of the still hot reaction mixture
  2. concentrationthe filtrate is concentrated in vacuo
  3. dissolutionthe solid residue is dissolved in 250 ml of 2N sodium hydroxide solution
  4. addition2N hydrochloric acid is added
  5. temperatureAfter cooling
  6. customthe solid formed
  7. filtrationis filtered off under suction
  8. washwashed salt-free with water
  9. washrinsed with methanol
  10. customdried in vacuo

Sources & evidence

ORD record
ord-aba8994c21544bfc83f881a0b0145030
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

Loading…