Hydrochloric Acid → 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[2-(3-piperidinyl)ethyl]-7,9-dihydro-8H-purin-8-one

HRID 1044976Notes

Reaction equation

HRID 1044976 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:24]C)[N:13]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[C:9]([NH2:26])[N:8]=1)[CH2:3][CH2:4][CH3:5].Cl.O1CCOCC1>CO>[NH2:26][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:24])[N:13]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 583060842-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine

Product 1

HCID 672344106-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[2-(3-piperidinyl)ethyl]-7,9-dihydro-8H-purin-8-oneYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine (35 mg, 0.097 mmol) in methanol (4 ml) was added 4M HCl in dioxane (1.5 ml, 6.00 mmol) and the mixture was allowed to stir at room temperature for 1.5 hours. The reaction was then dried under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. This was redissolved in methanol (˜5 mL) and passed down a 2 g aminopropyl (—NH2) SPE cartridge. The filtrate was dried under a stream of nitrogen in Radleys blowdown apparatus. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound as an off-white solid (21.5 mg). LCMS (System D): tRET=2.25 min; MH+ 349

Workup

  1. customThe reaction was then dried under a stream of nitrogen in the Radleys blowdown apparatus
  2. customto give the crude product
  3. customThe filtrate was dried under a stream of nitrogen in Radleys blowdown apparatus
  4. dissolutionThe sample was dissolved in 1:1 MeOH
  5. customDMSO (1 ml) and purified by Mass Directed AutoPrep (Method A)
  6. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-2d9641296d2640258c12f74a266dad93
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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