Propylamine → 6-Amino-9-benzyl-2-propylaminopurine

HRID 2269114Notes

Reaction equation

HRID 2269114 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([NH2:22])[CH2:20][CH3:21].[OH-].[Na+]>CO>[NH2:1][C:2]1[N:10]=[C:9]([NH:22][CH2:19][CH2:20][CH3:21])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 183327076-Amino-9-benzyl-2-propylaminopurineYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (10 mg, 0.385 mmol) and propylamine (228 mg, 3.85 mmol) in methanol (50 ml) were heated at 120° C. for 10 hours in autoclave. The reaction mixture was condensed in vacuo and to the residue was added 5N aqueous sodium hydroxide, followed by extraction with chloroform. The organic layer was dried on sodium sulfate, filtered and the solvent in the filtrate was evaporated in vacuo. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (99 mg, yield 91%).

Workup

  1. customcondensed in vacuo
  2. extractionfollowed by extraction with chloroform
  3. customThe organic layer was dried on sodium sulfate
  4. filtrationfiltered
  5. customthe solvent in the filtrate was evaporated in vacuo
  6. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-3b674e855725474fb8595f9e7148f985
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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