Hydrochloric Acid → 6-Amino-2-(butylamino)-9-[4-(tetrahydro-2H-pyran-3-yl)butyl]-7,9-dihydro-8H-purin-8-one

HRID 1011194Notes

Reaction equation

HRID 1011194 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:25]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][O:21][CH2:20]2)=[C:8]([NH2:27])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1.[OH-].[Na+]>CO>[NH2:27][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:25])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][O:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 57699752N2-butyl-8-(methoxy)-9-[4-(tetrahydro-2H-pyran-3-yl)butyl]-9H-purine-2,6-diamine

Product 1

HCID 576996916-Amino-2-(butylamino)-9-[4-(tetrahydro-2H-pyran-3-yl)butyl]-7,9-dihydro-8H-purin-8-oneYield 51.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N2-butyl-8-(methoxy)-9-[4-(tetrahydro-2H-pyran-3-yl)butyl]-9H-purine-2,6-diamine (172 mg) in methanol (15.2 ml) at room temperature was added 4.0M hydrogen chloride in 1,4-dioxane (2.86 ml, 11.42 mmol) to give a colourless solution. The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was neutralised with 2M NaOH and concentrated in vacuo to give a white solid. This solid was triturated in water and filtered under vacuum to give an off-white solid (85 mg).

Workup

  1. customto give a colourless solution
  2. concentrationconcentrated in vacuo
  3. customto give a white solid
  4. customThis solid was triturated in water
  5. filtrationfiltered under vacuum

Sources & evidence

ORD record
ord-b30595f941844e11a796d50292bc5ed9
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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