Benzylamine → HCID 18332705, compound

HRID 2269119Notes

Reaction equation

HRID 2269119 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]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[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 7504BenzylamineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332705HCID 18332705, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) and benzylamine (825 mg, 7.70 mmol) in 1-butanol (10 ml) were refluxed on heating for 8 hours. The reaction mixture was condensed in vacuo. To the residue was added 5N aqueous sodium hydroxide and the solution was extracted 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 (171 mg, yield 67%).

Workup

  1. temperatureon heating for 8 hours
  2. customcondensed in vacuo
  3. extractionthe solution was extracted with chloroform
  4. customThe organic layer was dried on sodium sulfate
  5. filtrationfiltered
  6. customthe solvent in the filtrate was evaporated in vacuo
  7. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-ed56bb11332d4d01b0deccf8da45aef6
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

Loading…