Benzyl Alcohol → HCID 18440616, compound

HRID 457693Notes

Reaction equation

HRID 457693 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH2:13])[N:3]=1.[OH-].[Na+].[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH2:13])[N:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 232737382-Chloro-9-ethyl-9H-purin-6-amine

Product 1

HCID 18440616HCID 18440616, compound

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-chloro-9-ethyl-9H-purin-6-ylamine (0.2 g, 1.01 mmol), a compound of formula (3), and dry sodium hydroxide (5 mmol) was added benzyl alcohol (9.0 mmol). This mixture was heated at 85° C. for 3 hours. The solvent was then removed under reduced pressure and the residue was neutralized with 2N HCl and extracted with CHCl3. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on a silica gel column eluting with a mixture of ethyl acetate/cyclohexane/methanol (60/33/5) to give 2-benzyloxy-9-ethyl-9H-purin-6-ylamine as a chromatographically pure solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with a mixture of ethyl acetate/cyclohexane/methanol (60/33/5)

Sources & evidence

ORD record
ord-fd86049b54c34effaceb3e5f72791067
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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