Hydrochloric Acid → HCID 9882178, compound

HRID 1835726Notes

Reaction equation

HRID 1835726 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[C:14](=[N:15][N:16]([CH3:21])[N:17]=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[C:18](=[N:17][N:16]([CH3:21])[N:15]=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 69752229HCID 69752229, compound

Product 1

HCID 9882178HCID 9882178, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(5-acetoxyhexyl)-3,8-dimethyl-8-azaxanthine (66 mg, 0.204 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)-3,8-dimethyl-1-(5-hydroxyhexyl)-8-azaxanthine (37 mg, 65% 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-548ddab6119d406b914bbf8b35a75b94
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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