Hydrochloric Acid → HCID 10221356, compound

HRID 1835725Notes

Reaction equation

HRID 1835725 reaction equation
C([O:4][C@H:5]([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[N:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])(=O)C.Cl.C(OCC)C>CO>[CH3:22][N:13]1[C:14]2[N:15]=[N:16][N:17]([CH3:21])[C:18]=2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:23])[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54318714HCID 54318714, compound

Product 1

HCID 10221356HCID 10221356, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(5-acetoxyhexyl)-3,7-dimethyl-8-azaxanthine (71 mg, 0.22 mmol) in methanol (15 ml) was added an anhydrous solution of hydrogen chloride in ethyl ether (1 M, 1.0 ml, 1.0 mmol). The mixture was stirred at room temperature for 24 hours and then the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-methanol (7:1) to provide (R)-3,7-dimethyl-1-(5-hydroxyhexyl)-8-azaxanthine (CT 12464) (55 mg, 88% yield) as a white solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-methanol (7:1)

Sources & evidence

ORD record
ord-bae45f799d5f4a54a43b251c96063f72
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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