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

HRID 1011208Notes

Reaction equation

HRID 1011208 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:23]C)[N:13]3[CH2:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)=[C:9]([NH2:25])[N:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[NH2:25][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:23])[N:13]2[CH2:16][CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][O:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 576997792-[(2-Cyclopropylethyl)oxy]-8-(methyloxy)-9-[2-(tetrahydro-2-furanyl)ethyl]-9H-purin-6-amine

Product 1

HCID 250263586-Amino-2-[(2-cyclopropylethyl)oxy]-9-[2-(tetrahydro-2-furanyl)ethyl]-7,9-dihydro-8H-Purin-8-oneYield 48.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-9-[2-(tetrahydro-2-furanyl)ethyl]-9H-purin-6-amine (88 mg, 0.253 mmol) in methanol (10 ml) at room temperature was added 4M HCl in 1,4 dioxane (2.106 ml, 8.42 mmol) to give a pale straw coloured solution. The reaction mixture was stirred at ambient temperature overnight (16 hours) and then loaded in methanol onto a 5 g aminopropyl SPE cartridge and eluted with methanol. The filtrate was evaporated on a nitrogen blowdown unit to give the title compound as a white solid (41 mg).

Workup

  1. customto give a pale straw coloured solution
  2. washeluted with methanol
  3. customThe filtrate was evaporated on a nitrogen

Sources & evidence

ORD record
ord-6add2e3876274f36a01c3d6d738b4446
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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