4-Butylaniline → 6H-Purin-6-one, 1,7-dihydro-2-((4-butylphenyl)amino)-

HRID 978303Notes

Reaction equation

HRID 978303 reaction equation
Br[C:2]1[NH:3][C:4](=[O:11])[C:5]2[NH:6][CH:7]=[N:8][C:9]=2[N:10]=1.[CH2:12]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15]>COCCO.O>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([NH:20][C:2]2[NH:3][C:4](=[O:11])[C:5]3[NH:6][CH:7]=[N:8][C:9]=3[N:10]=2)=[CH:21][CH:22]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 76944-ButylanilineHCID 1354139912-Bromohypoxanthine

Product 1

HCID 1354350846H-Purin-6-one, 1,7-dihydro-2-((4-butylphenyl)amino)-Yield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

A stirred solution of 2-bromohypoxanthine (10.8 g, 50 mmol) and p-n-butylaniline (23.5 mL, 150 mmol) in a mixture of 2-methoxyethanol (300 mL) and water (100 mL) was heated at reflux. After 2.5 h, the mixture was chilled in an ice bath, and the fine precipitate was filtered, washed with concentrated aqueous ammonia (80 mL) and methanol (3×25 mL). The product was purified by dissolving the slightly yellow precipitate in hot N sodium hydroxide (300 mL) and treatment with activated charcoal. The hot mixture was filtered, acidified with glacial acetic acid and chilled. The product was isolated by filtration, washed with methanol and dried over phosphorus pentoxide to yield 12.0 g (85%) of fine colorless crystals, identical with an authentic sample. NMR (250 MHz; Me2SO-d6) 10.45 δ(s, 1-H), 8.60 δ(s, 2-NH), 8.00 δ(s, 8-H), 7.50 δ(d, J+8.5 Hz, 2',6'-H), 7.14 δ(d, J=8.5 Hz, 3',5'-H), 2.55 δ(t, CH2), 1.56 δ(quin, CH2), 1.33 δ(sext, CH2), 0190 δ(t, CH3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture was chilled in an ice bath
  4. filtrationthe fine precipitate was filtered
  5. washwashed with concentrated aqueous ammonia (80 mL) and methanol (3×25 mL)
  6. customThe product was purified
  7. dissolutionby dissolving the slightly yellow precipitate in hot N sodium hydroxide (300 mL) and treatment with activated charcoal
  8. filtrationThe hot mixture was filtered
  9. temperaturechilled
  10. customThe product was isolated by filtration
  11. washwashed with methanol
  12. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-bcd176bf05b2423db282912d5eb46881
Source dataset
uspto-grants-1987_05
Patent number
US04663446

Reaction notes

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