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Hydrochloric Acid → 6-Amino-2-{[2-(ethyloxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011182
Notes
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Reaction equation

HRID 1011182 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:23]C)[N:13]2[CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][O:19][CH2:18]2)=[C:9]([NH2:25])[N:8]=1)[CH3:2].Cl.[OH-].[Na+]>CO.O1CCOCC1.O>[NH2:25][C:9]1[N:8]=[C:7]([O:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:23])[N:13]2[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][O:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576997302-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576997086-Amino-2-{[2-(ethyloxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-Purin-8-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine (245 mg) in dry methanol (10 ml) at room temperature and under nitrogen was added 4.0M hydrogen chloride in 1,4-dioxane (4.0 ml). The reaction was left to stir at room temperature for 1 hour. The reaction was concentrated in vacuo and the resulting residue purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (10-45%) to afford a white solid. This was taken up in water (15 ml) and neutralised by the addition of 2.0M sodium hydroxide solution. The solid was filtered and dried on the rotary evaporator (60° C.) for 30 minutes (90 mg).

Workup

  1. waitThe reaction was left
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe resulting residue purified by C18 reverse phase chromatography
  4. customto afford a white solid
  5. filtrationThe solid was filtered
  6. customdried on the rotary evaporator (60° C.) for 30 minutes (90 mg)

Sources & evidence

ORD record
ord-341d3d07536d428aaffa0398c1a950cc
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977344B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes