Cyclohexylamine → HCID 18332744, compound

HRID 2269120Notes

Reaction equation

HRID 2269120 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.[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:25][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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 7965CyclohexylamineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332744HCID 18332744, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) and cyclohexylamine (764 mg, 7.70 mmol) in 1-butanol (10 ml) were refluxed on heating for 60 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 (115 mg, yield 46%).

Workup

  1. temperatureon heating for 60 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-0fb7c59520624343a9c7cfbba911f10a
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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