Phenol → 8-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 984818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984818
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=2[N:10]=[C:9]1[N:21]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([NH:28]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.CCOC(C)=O>Br.C1C=CC=CC=1>[NH2:28][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][N:21]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]3[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=3[N:10]=2)[CH2:22]1

Komponenten

6

Edukt 3

HCID 996PhenolHCID 8857Ethyl AcetateHCID 22508573N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide

Produkt 1

HCID 101345098-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide (6C) (100 mg, 0.19 mmol) was dissolved in hydrobromic acid (48%, 5 ml) and benzene (0.07 ml), and phenol (61.4 mg, 0.65 mmol) was added. The mixture was heated to reflux for three hours, and after cooling 20 ml of EtOAc was added. The layers were separated, and the aqueous layer washed with 20 ml of EtOAc. pH was adjusted to 11 with 10M sodium hydroxide. The aqueous layer was extracted with diethyl ether (3×20 ml), and the combined organic layers were dried over sodium sulphate and the solvent was evaporated. The crude product was dissolved in 5 ml of DCM and 0.5 ml of trifluoroacetic acid was added. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=7.63 min). Evaporation of the solvent gave the title compound as an oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for three hours
  3. additionwas added
  4. customThe layers were separated
  5. washthe aqueous layer washed with 20 ml of EtOAc
  6. extractionThe aqueous layer was extracted with diethyl ether (3×20 ml)
  7. dry with materialthe combined organic layers were dried over sodium sulphate
  8. customthe solvent was evaporated
  9. dissolutionThe crude product was dissolved in 5 ml of DCM
  10. addition0.5 ml of trifluoroacetic acid was added
  11. customThe solvents were evaporated
  12. customthe crude product was purified by preparative HPLC (method A1, Rt=7.63 min)
  13. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-daa9c3ca060c420fbe25ca700d3b5cdb
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869947B2

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