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

HRID 1011180Notes

Reaction equation

HRID 1011180 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][O:20][CH2:19][CH2:18]2)=[C:9]([NH2:25])[N:8]=1)[CH3:2].Cl.[OH-].[Na+]>CO.O1CCOCC1>[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[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576995812-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576997946-Amino-2-{[2-(ethyloxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-oneYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (240 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 3 hours. The reaction was neutralised by the addition of 2.0M sodium hydroxide solution and concentrated in vacuo. The residue was taken up in water (15 ml) and the solid filtered and washed with water (2×5 ml). The solid was dried en vacuo (60° C.) for 30 minutes. This afforded the title compound as an off-white solid (129 mg).

Workup

  1. waitThe reaction was left
  2. concentrationconcentrated in vacuo
  3. filtrationthe solid filtered
  4. washwashed with water (2×5 ml)
  5. customThe solid was dried en vacuo (60° C.) for 30 minutes

Sources & evidence

ORD record
ord-0bac7af3194448e38047581f6f35b060
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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