Hydrochloric Acid → 6-Amino-2-[(2-cyclopropylethyl)oxy]-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-7,9-dihydro-8H-purin-8-one

HRID 1011209Notes

Reaction equation

HRID 1011209 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[C:12]([O:24]C)[N:13]3[CH2:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:9]([NH2:26])[N:8]=2)[CH2:3][CH2:2]1.Cl>CO.O1CCOCC1>[NH2:26][C:9]1[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[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][CH2:20][O:19]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57699626HCID 57699626, compound

Product 1

HCID 250261606-Amino-2-[(2-cyclopropylethyl)oxy]-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-7,9-dihydro-8H-purin-8-oneYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-9H-purin-6-amine (84.7 mg, 0.234 mmol) in methanol (7.9 ml) at room temperature was added 4.0 M HCl in 1,4-dioxane (1.46 ml) to give a pale straw coloured solution. The reaction mixture was stirred at ambient temperature overnight (20 hours) and then evaporated in vacuo to give a colourless oil/gum. This material was re-dissolved in methanol and passed down a 5 g aminopropyl SPE cartridge (pre-conditioned in methanol), washed through with methanol and evaporated to give the title compound as a white solid (58.5 mg).

Workup

  1. customto give a pale straw coloured solution
  2. customevaporated in vacuo
  3. customto give a colourless oil/gum
  4. washwashed through with methanol
  5. customevaporated

Sources & evidence

ORD record
ord-4f258210e6204b68ad7f165af823964e
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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