Trifluoroacetic acid → HCID 54426005, compound

HRID 1814970Notes

Reaction equation

HRID 1814970 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:37])[C@H:10]([CH3:36])[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[NH:22][C:21]([CH2:26][NH:27]C(OC(C)(C)C)=O)=[N:20][C:19]=2[N:18]([CH3:35])[C:16]1=[O:17]>ClCCl>[CH3:37][N:9]([CH3:8])[C@H:10]([CH3:36])[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[NH:22][C:21]([CH2:26][NH2:27])=[N:20][C:19]=2[N:18]([CH3:35])[C:16]1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20773488HCID 20773488, compound

Product 1

HCID 54426005HCID 54426005, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50% solution of trifluoroacetic acid in dichloromethane (15 ml) was added (R)-1-(5-dimethylaminohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.16 g, 0.38 mmol). After stirring at room temperature for 3 hours, the solvent and excess reagent were evaporated under reduced pressure. The residue was treated with ammonia-methanol solution (2.0 M, 10 ml) and stirred for 1 hour. Concentration under reduced pressure gave the crude product which was purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate (2:10:1). (R)-1-(5-Dimethylaminohexyl)-8-aminomethyl-3-methylxanthine (0.062 g, 50% yield) was obtained as an oil.

Workup

  1. customthe solvent and excess reagent were evaporated under reduced pressure
  2. additionThe residue was treated with ammonia-methanol solution (2.0 M, 10 ml)
  3. stirringstirred for 1 hour
  4. concentrationConcentration under reduced pressure
  5. customgave the crude product which
  6. customwas purified by flash chromatography on silica gel eluting with ammonium hydroxide (37% in water)-methanol-ethyl acetate (2:10:1)

Sources & evidence

ORD record
ord-c1c338f40c104fe4bccdaa70730f01e5
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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