Pentylamine → HCID 18332766, compound

HRID 2269115Notes

Reaction equation

HRID 2269115 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]([NH2:24])[CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:24][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[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 8060PentylamineHCID 14798Sodium HydroxideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332766HCID 18332766, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

6-Amino-9-benzyl-2-chloropurine (100 mg, 0.385 mmol) and pentylamine (336 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 (83 mg, yield 70%).

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-9f603b90f4b24e6897be97bb47f166f7
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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