Hydrochloric Acid → 6-Amino-9-[3-(1-azetidinyl)propyl]-2-(butyloxy)-7,9-dihydro-8H-purin-8-one

HRID 1616320Notes

Reaction equation

HRID 1616320 reaction equation
[N:1]1([CH2:5][CH2:6][CH2:7][N:8]2[C:16]([O:17]C)=[N:15][C:14]3[C:9]2=[N:10][C:11]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:12][C:13]=3[NH2:19])[CH2:4][CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[NH2:19][C:13]1[N:12]=[C:11]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:10]=[C:9]2[C:14]=1[NH:15][C:16](=[O:17])[N:8]2[CH2:7][CH2:6][CH2:5][N:1]1[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 592526009-[3-(1-Azetidinyl)propyl]-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine

Product 1

HCID 592526036-Amino-9-[3-(1-azetidinyl)propyl]-2-(butyloxy)-7,9-dihydro-8H-purin-8-oneYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9-[3-(1-Azetidinyl)propyl]-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine (13 mg, 0.039 mmol) was dissolved in methanol (3 ml) and 4M hydrogen chloride in 1,4-dioxane (0.243 ml, 0.972 mmol) was added and the mixture stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was dissolved in methanol and loaded onto an aminopropyl SPE cartridge (2 g). The cartridge was eluted with methanol and the solvent removed to give the title compound as a white solid (13 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol
  3. washThe cartridge was eluted with methanol
  4. customthe solvent removed

Sources & evidence

ORD record
ord-b4211a45e168433a8e61069b1dc4f0e2
Source dataset
uspto-grants-2014_07
Patent number
US08765772B2

Reaction notes

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