Hydrochloric Acid → 6-Amino-2-{[(1R)-1-methylbutyl]oxy}-9-[3-(tetrahydro-3-furanyl)propyl]-7,9-dihydro-8H-purin-8-one

HRID 1011211Notes

Reaction equation

HRID 1011211 reaction equation
[CH3:1][C@@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:24]C)[N:13]2[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[C:9]([NH2:26])[N:8]=1)[CH2:3][CH2:4][CH3:5].Cl.O1CCOCC1>CO>[NH2:26][C:9]1[N:8]=[C:7]([O:6][C@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:24])[N:13]2[CH2:16][CH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][O:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 576997402-{[(1R)-1-methylbutyl]oxy}-8-(methyloxy)-9-[3-(tetrahydro-3-furanyl)propyl]-9H-purin-6-amine

Product 1

HCID 250247736-Amino-2-{[(1R)-1-methylbutyl]oxy}-9-[3-(tetrahydro-3-furanyl)propyl]-7,9-dihydro-8H-purin-8-oneYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-{[(1R)-1-methylbutyl]oxy}-8-(methyloxy)-9-[3-(tetrahydro-3-furanyl)propyl]-9H-purin-6-amine (52 mg, 0.143 mmol) in methanol (5 ml) at room temperature was added 4M HCl in dioxane (0.894 ml, 3.58 mmol). The reaction mixture was stirred at room temperature for 18 hrs and concentrated in vacuo to give a white solid. This material was dissolved in methanol and loaded onto a 2 g aminopropyl SPE cartridge, eluting with methanol. The solvent was removed to give the title compound as a white solid (36 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a white solid
  3. washeluting with methanol
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-1244044518424cdb9d17dc132078c285
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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