Aniline → HCID 18332798, compound

HRID 2269121Notes

Reaction equation

HRID 2269121 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.[NH2:19][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: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 6115AnilineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332798HCID 18332798, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (100 mg, 0.385 mmol) and aniline (359 mg, 3.85 mmol) in 1-butanol (10 ml) were refluxed on heating for 20 hours. The reaction mixture was condensed in vacuo. To the residue was added 5N aqueous sodium hydroxide and the mixture 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 (108 mg, yield 89%).

Workup

  1. temperatureon heating for 20 hours
  2. customcondensed in vacuo
  3. extractionthe mixture 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-eb177b8cedf34a86b267f511437e0e20
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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