Hydrochloric Acid → 6-Amino-2-({2-[(1-methylethyl)oxy]ethyl}oxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011193Notes

Reaction equation

HRID 1011193 reaction equation
[CH3:1][CH:2]([O:4][CH2:5][CH2:6][O:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[C:13]([O:24]C)[N:14]2[CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:10]([NH2:26])[N:9]=1)[CH3:3].Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:26][C:10]1[N:9]=[C:8]([O:7][CH2:6][CH2:5][O:4][CH:2]([CH3:3])[CH3:1])[N:16]=[C:15]2[C:11]=1[NH:12][C:13](=[O:24])[N:14]2[CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57699826HCID 57699826, compound

Product 1

HCID 576996306-Amino-2-({2-[(1-methylethyl)oxy]ethyl}oxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-({2-[(1-methylethyl)oxy]ethyl}oxy)-8-(methoxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (165 mg) in dry methanol (17 ml) was added 4.0M hydrogen chloride in 1,4-dioxane (2.95 ml) in one go. The reaction was left to stir at room temperature for 5 hours. The reaction was neutralised by the addition of 2.0M sodium hydroxide solution and concentrated in vacuo to give an off-white solid. The solid was triturated in water, and filtered under vacuum, washing with more water, to give an off-white solid (120 mg).

Workup

  1. waitThe reaction was left
  2. concentrationconcentrated in vacuo
  3. customto give an off-white solid
  4. customThe solid was triturated in water
  5. filtrationfiltered under vacuum
  6. washwashing with more water

Sources & evidence

ORD record
ord-0ed9fc2681fa470e9b07396cb2458a41
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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