Hydrochloric Acid → HCID 178462272, compound

HRID 1835723Notes

Reaction equation

HRID 1835723 reaction equation
C([O:4][C@H:5]([CH3:22])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][N:16]=[N:15][C:14]=2[N:13]([CH3:21])[C:11]1=[O:12])(=O)C.Cl.C(OCC)C>CO>[OH:4][C@H:5]([CH3:22])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][N:16]=[N:15][C:14]=2[N:13]([CH3:21])[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178476621HCID 178476621, compound

Product 1

HCID 178462272HCID 178462272, compoundYield 11,020.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of (R)-1-(5-acetoxyhexyl)-3-methyl-8-azaxanthine (150 mg, 0.49 mmol) in methanol (25 ml) was added an anhydrous solution of hydrogen chloride in ethyl ether (1 M, 1.0 ml, 1.0 mmol). After stirring at room temperature for 24 hours, 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)-1-(5-hydroxyhexyl)-3-methyl-8-azaxanthine (CT 12463) (70 mg, 54 mmol) 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-243c8781874e4a12a888f5321f299c15
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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