Hydrochloric Acid → 6-Amino-2-(butyloxy)-9-{3-[(tetrahydro-3-furanylmethyl)amino]propyl}-7,9-dihydro-8H-purin-8-one

HRID 2036366Notes

Reaction equation

HRID 2036366 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:25]C)[N:12]2[CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)=[C:8]([NH2:27])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1>CO>[NH2:27][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:25])[N:12]2[CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH:20]1[CH2:24][CH2:23][O:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67224141HCID 67224141, compound

Product 1

HCID 672115066-Amino-2-(butyloxy)-9-{3-[(tetrahydro-3-furanylmethyl)amino]propyl}-7,9-dihydro-8H-purin-8-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(Butyloxy)-8-(methyloxy)-9-{3-[(tetrahydro-3-furanylmethyl)amino]propyl}-9H-purin-6-amine (11 mg, 0.029 mmol) and 4M HCl in 1,4 dioxane (0.160 ml, 0.639 mmol) were stirred at 20° C. for 16 hours in methanol (1 ml). The solvent was removed by N2 blowdown. The sample was loaded in methanol and purified by SPE on an aminopropyl (NH2) cartridge (2 g) using methanol. The appropriate fractions were combined and dried under a stream of nitrogen to give the crude product as a white solid. The sample were dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound as a white solid (5.6 mg).

Workup

  1. customThe solvent was removed by N2
  2. custompurified by SPE on an aminopropyl (NH2) cartridge (2 g)
  3. customdried under a stream of nitrogen
  4. customto give the crude product as a white solid
  5. customDMSO (1 ml) and purified by Mass Directed AutoPrep (Method A)
  6. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-245b607e6d2247e9803acedea409e7aa
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

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