Isobutylamine → HCID 18332778, compound

HRID 2269116Notes

Reaction equation

HRID 2269116 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]([NH2:23])[CH:20]([CH3:22])[CH3:21].[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:23][CH2:19][CH:20]([CH3:22])[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 6558IsobutylamineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332778HCID 18332778, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

6-Amino-9-benzyl-2-chloropurine (100 mg, 0.385 mmol) and isobutylamine (288 mg, 3.85 mmol) suspended in 1-butanol (10 ml) were heated at 100° C. for 10 hours in autoclave. The reaction mixture was condensed in vacuo. To the residue was added 1N 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 (89 mg, yield 78%).

Workup

  1. customcondensed in vacuo
  2. extractionthe solution was extracted 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-7e61bddaca6e40868b76879145a73a68
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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