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

HRID 1011181Notes

Reaction equation

HRID 1011181 reaction equation
[CH3:1][CH:2]([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)[CH2:3][O:4][CH3:5].Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:25][C:9]1[N:8]=[C:7]([O:6][CH:2]([CH3:1])[CH2:3][O:4][CH3:5])[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 576998202-{[1-Methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576997566-Amino-2-{[1-methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-oneYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-{[1-methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (260 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 (70 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-ae59c18ee53e49d282a8d12c9719c974
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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