Potassium Carbonate → 8-{[2-(6-Fluoropyridin-2-yl)-1H-imidazol-1-yl]methyl}-2,9-dimethyl-9H-purine

HRID 1988778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988778
Cl[CH2:2][C:3]1[N:4]([CH3:13])[C:5]2[C:10]([N:11]=1)=[CH:9][N:8]=[C:7]([CH3:12])[N:6]=2.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)[N:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:14][C:15]1[N:16]=[C:17]([C:21]2[N:25]([CH2:2][C:3]3[N:4]([CH3:13])[C:5]4[C:10]([N:11]=3)=[CH:9][N:8]=[C:7]([CH3:12])[N:6]=4)[CH:24]=[CH:23][N:22]=2)[CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223799558-Chloromethyl-2,9-dimethyl-9H-purine

Produkt 1

HCID 223799438-{[2-(6-Fluoropyridin-2-yl)-1H-imidazol-1-yl]methyl}-2,9-dimethyl-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 8-Chloromethyl-2,9-dimethyl-9H-purine (40 mg, 0.2 mmol), 2-Fluoro-6-(1H-imidazol-2-yl)-pyridine (40 mg, 0.25 mmol) and K2CO3 (55 mg, 0.4 mmol) in 2 mL of DMF is stirred at room temperature for four hours. The mixture is diluted with water (10 mL), and extracted with ethyl acetate three times. The combined extract is washed with brine, dried and concentrated. The residue is purified by preparative thin layer chromatography to give the title compound. 1H NMR (CDCl3): δ 8.92 (s, 1H), 8.18 (dd, 1H), 7.88 (q, 1H), 7.25 (s, 1H), 7.20 (s, 1H), 7.11 (s, 1H), 6.83 (dd, 1H), 6.22 (s, 2H), 3.89 (s, 3H), 2.8 (s, 3H). LRMS calcd 323. found 324 (MH+).

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. extractionThe combined extract
  3. washis washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f400a0e156f54b459fa49a937979574c
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642267B2

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