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Hydrochloric Acid → 6-Amino-2-butoxy-9-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-7,9-dihydro-8H-Purin-8-one

HRID 1011156
Notes
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Reaction equation

HRID 1011156 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:23]C)[N:12]2[CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[C:8]([NH2:25])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O.[OH-].[Na+]>CO.O1CCOCC1>[NH2:25][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:23])[N:12]2[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 576997262-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-9H-purin-6-amine

Product 1

HCID 250251686-Amino-2-butoxy-9-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-7,9-dihydro-8H-Purin-8-oneYield 77.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-9H-purin-6-amine (0.11 g) 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 was 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 quantity of water remaining) and the solid thus obtained was filtered (transferred and washed the solid with water (3 mL)). The solid was dried under suction before being dried further in vacuo to afford the title compound as a white solid (82 mg).

Workup

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

Sources & evidence

ORD record
ord-29a35715e40c460b8ea1ad691bfe741c
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977344B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes