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

HRID 1011170Notes

Reaction equation

HRID 1011170 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:22]C)[N:13]3[CH2:16][CH:17]3[CH2:21][CH2:20][O:19][CH2:18]3)=[C:9]([NH2:24])[N:8]=2)[CH2:3][CH2:2]1.Cl.O.[OH-].[Na+]>CO.O1CCOCC1>[NH2:24][C:9]1[N:8]=[C:7]([O: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:22])[N:13]2[CH2:16][CH:17]1[CH2:21][CH2:20][O:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 576996582-[(2-Cyclopropylethyl)oxy]-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amine

Product 1

HCID 250240096-Amino-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-3-furanylmethyl)-7,9-dihydro-8H-purin-8-oneYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(2-cyclopropylethyl)oxy]-8-methoxy-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amine (103.8 mg) in methanol (5 mL) was added 4N HCl in 1,4-dioxane (2 mL) and the reaction mixture was stirred at room temperature for 4 h. The reaction was evaporated under reduced pressure to give a gum. Water (3 mL) was added to give a white solid. The mixture was adjusted to pH 7 by adding 2N sodium hydroxide solution and the white solid was filtered off under suction, then washed with a few drops of MeOH. The material was air dried under suction, then in a vacuum oven (50° C.) to give the title compound as white solid (77 mg).

Workup

  1. customThe reaction was evaporated under reduced pressure
  2. customto give a gum
  3. customto give a white solid
  4. filtrationthe white solid was filtered off under suction
  5. washwashed with a few drops of MeOH
  6. customdried under suction

Sources & evidence

ORD record
ord-f35637b4f0c94c3c849b3fd66a74253a
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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