1,3-Dibutylxanthine → HCID 11406633, compound

HRID 1943818Notes

Reaction equation

HRID 1943818 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].C1C(=O)N([I:27])C(=O)C1>CN(C=O)C>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11]([I:27])=[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

4

Reactant 2

HCID 1014211,3-DibutylxanthineHCID 120273N-Iodosuccinimide

Product 1

HCID 11406633HCID 11406633, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1,3-di-N-butyl xanthine (100 mg, 3.39 mmol) in anhydrous DMF (3 ml) was treated with NIS (94 mg, 3.75 mmol) and left to stir at rt. under nitrogen for 23 hours. The mixture was partitioned between sat. Na2SO3 (aq) solution and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The product was purified by passing down an SPE (Si, 5 g) cartridge eluting with EtOAc/cyclohexane mixtures. The product fraction was concentrated to afford the title compound as a white solid (75 mg, 51%); NMR; δH (400 MHz, d6-DMSO) (app. td, 6H, J=7.5 and 4 Hz), 1.21-1.34 (m, 4H), 1.45-1.54 (m, 2H), 1.56-1.66 (m, 2H), 3.84 (t, 2H, J=7.5 Hz), 3.93 (t, 2H, J=7.5 Hz), 14.10 (s, 1H); m/z 391.3[MH+].

Workup

  1. waitleft
  2. customThe mixture was partitioned between sat. Na2SO3 (aq) solution and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe product was purified
  8. washeluting with EtOAc/cyclohexane mixtures
  9. concentrationThe product fraction was concentrated

Sources & evidence

ORD record
ord-b6e8791548a34475a21b44fb61438172
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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