Hydrochloric Acid → 6-Amino-2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011166Notes

Reaction equation

HRID 1011166 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][CH2:4][CH3:5].Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:25][C:9]1[N:8]=[C:7]([O:6][CH:2]([CH3:1])[CH2:3][CH2:4][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 576997382-[(1-Methylbutyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

Product 1

HCID 250255556-Amino-2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(1-methylbutyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (92 mg) in dry MeOH (9.9 mL) was added 4N HCl in 1,4-dioxane (1.7 mL) and the reaction mixture was stirred at room temperature for 3 h. The reaction was neutralised to pH7 with 2M sodium hydroxide solution and concentrated in vacuo to give an off-white solid. The solid was triturated with water (30 mL) and filtered under reduced pressure to give the title compound as an off-white solid (55 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an off-white solid
  3. customThe solid was triturated with water (30 mL)
  4. filtrationfiltered under reduced pressure

Sources & evidence

ORD record
ord-462b0c18767d490b94658a8f4cbf3cb3
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…