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

HRID 1011162Notes

Reaction equation

HRID 1011162 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:24][CH2:25][CH3:26])[CH2:3][O:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[C:10]([O:21]C)[N:11]2[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:7]([NH2:23])[N:6]=1.Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:23][C:7]1[N:6]=[C:5]([O:4][CH2:3][C:2]([CH3:1])([CH3:27])[CH2:24][CH2:25][CH3:26])[N:13]=[C:12]2[C:8]=1[NH:9][C:10](=[O:21])[N:11]2[CH2:14][CH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576996372-[(2,2-Dimethylpentyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

Product 1

HCID 250253646-Amino-2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(2,2-dimethylpentyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (116 mg) in dry MeOH (14.5 mL) was added 4N HCl in 1,4-dioxane (2.48 mL). The mixture was stirred at room temperature for 3 h. The reaction was neutralised to pH 7 with 2M sodium hydroxide solution and was concentrated in vacuo to give and off-white solid. The solid was triturated with water (30 mL) and was filtered under reduced pressure to give the title compound as an off-white solid (76 mg).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give
  3. customThe solid was triturated with water (30 mL)
  4. filtrationwas filtered under reduced pressure

Sources & evidence

ORD record
ord-2eb0a3461d824e318cb4116125f69468
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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