Hydrochloric Acid → 6-Amino-2-butoxy-9-(tetrahydrofuran-3-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011155Notes

Reaction equation

HRID 1011155 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21]C)[N:12]2[CH2:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O.[OH-].[Na+]>CO.O1CCOCC1>[NH2:23][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:21])[N:12]2[CH2:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

Product 1

HCID 250251676-Amino-2-butoxy-9-(tetrahydrofuran-3-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 66.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine (97 mg) was dissolved in methanol (2 mL) and treated with 4N hydrogen chloride in 1,4-dioxane (1 mL). The reaction mixture was stirred for 4 hours. The reaction was stripped to dryness. Water (2 mL) and methanol (15 mL) was added to the residue and then neutralised by the addition of 2N sodium hydroxide solution. The above was stripped to near dryness (small quantity of water remaining) and the solid thus obtained was filtered (transferred and washed the solid with water (2 mL, 3 times)). The solid was dried under suction before being dried further in vacuo (50° C.) for 2 hours. This afforded the title compound as a white solid (62 mg).

Workup

  1. customthe solid thus obtained
  2. filtrationwas filtered (
  3. washwashed the solid with water (2 mL, 3 times))
  4. customThe solid was dried under suction
  5. custombefore being dried further in vacuo (50° C.) for 2 hours

Sources & evidence

ORD record
ord-afed0e4e87804660bf79aeac07d30e11
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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