Hydrochloric Acid → 6-Amino-2-(butylamino)-9-[3-(tetrahydro-2H-pyran-3-yl)propyl]-7,9-dihydro-8H-Purin-8-one

HRID 1011192Notes

Reaction equation

HRID 1011192 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:24]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][O:20][CH2:19]2)=[C:8]([NH2:26])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.[OH-].[Na+].O>CO.O1CCOCC1>[NH2:26][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:24])[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][O:20][CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57699834HCID 57699834, compound

Product 1

HCID 576997136-Amino-2-(butylamino)-9-[3-(tetrahydro-2H-pyran-3-yl)propyl]-7,9-dihydro-8H-Purin-8-oneYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N2-butyl-8-(methoxy)-9-[3-(tetrahydro-2H-pyran-3-yl)propyl]-9H-purine-2,6-diamine (198 mg) in dry methanol (20.8 ml) was added 4.0M hydrochloric acid in 1,4-dioxane (3.6 ml) in one go. The reaction was left to stir at room temperature for 4 hours. The reaction was neutralised by the addition of 2.0M sodium hydroxide solution and concentrated in vacuo. to give an off-white solid. To this solid was added water, triturated, and the solid filtered under vacuum until dry. This afforded the title compound as an off-white solid (151 mg).

Workup

  1. waitThe reaction was left
  2. concentrationconcentrated in vacuo
  3. customto give an off-white solid
  4. customtriturated
  5. filtrationthe solid filtered under vacuum
  6. customuntil dry

Sources & evidence

ORD record
ord-392564edfd4d4e5e9e75192fd5fcc8b5
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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