Hydrochloric Acid → 6-Amino-2-[(2-cyclopropylethyl)amino]-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011196Notes

Reaction equation

HRID 1011196 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[C:12]([O:23]C)[N:13]3[CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][O:19][CH2:18]3)=[C:9]([NH2:25])[N:8]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:25][C:9]1[N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:23])[N:13]2[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][O:19][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57699575N2-(2-Cyclopropylethyl)-8-(methyloxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine

Product 1

HCID 576997646-Amino-2-[(2-cyclopropylethyl)amino]-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 59.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N2-(2-cyclopropylethyl)-8-(methoxy)-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine (198 mg) in methanol (19.1 ml) at room temperature was added 4.0M hydrogen chloride in 1,4-dioxane (3.57 ml) to give a colorless solution. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was neutralised with 2M NaOH and concentrated in vacuo. The resulting solid was taken up in water (50 ml) and filtered off to give a white solid. This solid was recrystallised from ethanol:water (1:1) and filtered to afford an off-white crystalline solid (113 mg).

Workup

  1. customto give a colorless solution
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered off
  4. customto give a white solid
  5. customThis solid was recrystallised from ethanol:water (1:1)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-587d0f0e21ad460a91dddd7ce233529a
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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