Hydrochloric Acid → 6-Amino-2-butoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011157Notes

Reaction equation

HRID 1011157 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:22]C)[N:12]2[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][O:18][CH2:17]2)=[C:8]([NH2:24])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O.[OH-].[Na+]>CO.O1CCOCC1>[NH2:24][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:22])[N:12]2[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][O:18][CH2:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 576996312-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine

Product 1

HCID 250251696-Amino-2-butoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-7,9-dihydro-8H-Purin-8-oneYield 71.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine (105 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 and stripped to dryness. Water (2 mL) and methanol (15 mL) were added to the residue and then neutralised by the addition of 2N sodium hydroxide solution. The above was stripped to near dryness (small volume of water remaining) and the solid thus obtained was filtered off under suction (transferred and washed with water (2 mL, 3 times)). The solid was dried under suction before being dried further in vacuo to afford the title compound as a white solid (71.5 mg).

Workup

  1. customthe solid thus obtained
  2. filtrationwas filtered off under suction (transferred and washed with water (2 mL, 3 times))
  3. customThe solid was dried under suction
  4. custombefore being dried further in vacuo

Sources & evidence

ORD record
ord-d6841a0a5aca4ac78c1835de04188d84
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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