Hydrochloric Acid → 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-7,9-dihydro-8H-purin-8-one

HRID 2036368Notes

Reaction equation

HRID 2036368 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:28]C)[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:9]([NH2:30])[N:8]=1)[CH2:3][CH2:4][CH3:5].Cl.O1CCOCC1>CO>[NH2:30][C:9]1[N:8]=[C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:28])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 672240132-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-9H-purin-6-amine

Product 1

HCID 446239386-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-7,9-dihydro-8H-purin-8-oneYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-9H-purin-6-amine (35.47 mg, 0.084 mmol) was stirred in methanol (2.3 ml) and treated with 4M HCl in 1,4 dioxane (0.527 ml, 2.109 mmol). The reaction was stirred in a capped vial overnight and then evaporated under nitrogen and the residue dissolved in 1:1 DMSO:MeOH (1 ml) and purified by Mass Directed AutoPrep (Method A). Product-containing fractions were combined and evaporated in a nitrogen blowdown unit to give the title compound as an off-white gum (23.28 mg).

Workup

  1. customevaporated under nitrogen
  2. dissolutionthe residue dissolved in 1:1 DMSO
  3. customMeOH (1 ml) and purified by Mass Directed AutoPrep (Method A)
  4. customevaporated in a nitrogen

Sources & evidence

ORD record
ord-1405582517434d31a4f455382bc2dbae
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

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