Allyl bromide → HCID 59299537, compound

HRID 1943813Notes

Reaction equation

HRID 1943813 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[CH2:26](Br)[CH:27]=[CH2:28]>CN(C=O)C>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[N:12]([CH2:28][CH:27]=[CH2:26])[CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1014211,3-Dibutylxanthine

Product 1

HCID 59299537HCID 59299537, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 1,3-di-N-butyl xanthine (10 g, 38 mmol) in anhydrous DMF (80 ml) was treated with K2CO3 (5.2 g, 38 mmol) followed by allyl bromide (3.6 ml, 42 mmol). The mixture was heated at 55° C. under nitrogen for 18 hours. After cooling to rt the mixture was partitioned between water and EtOAc. A few mls of 2M HCl (aq) was added to aid separation. The organic layer was separated and the aqueous extracted once more with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and concentrated to afford the title compound as an off-white solid (12.23 g, 106%). m/z 305.3[MH+].

Workup

  1. temperatureAfter cooling to rt the mixture
  2. customwas partitioned between water and EtOAc
  3. additionA few mls of 2M HCl (aq) was added
  4. customseparation
  5. customThe organic layer was separated
  6. extractionthe aqueous extracted once more with EtOAc
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7cd866a9faf44916a23a46c9f50b99b8
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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