6-Methoxy-3-pyridinylamine → HCID 66600240, Verbindung

HRID 1621374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621374
F[C:2]1[C:7]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:31][O:30][C:27]1[N:26]=[CH:25][C:24]([NH:23][C:2]2[C:7]([C:8]3[N:16]=[CH:15][N:14]=[C:13]4[C:9]=3[N:10]=[CH:11][N:12]4[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 811216-Methoxy-3-pyridinylamineHCID 2733832Lithium HexamethyldisilazideHCID 444791786-(2-Fluoropyridin-3-YL)-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

Produkt 1

HCID 66600240HCID 66600240, VerbindungAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (196.6 mg, 657 μmol) and 3-amino-6-methoxypyridine (Aldrich, St. Louis, Mo.) (101.9 mg, 821 μmol) in THF (2.0 mL) was cooled in an ice bath and treated with LiHMDS (3.0 mL, 3.0 mmol). A blood-red solution was obtained. The mixture was stirred for 1 h, and then quenched with water (0.1 mL). The mixture was extracted into EtOAc from saturated aqueous NaHCO3, concentrated and purified by flash chromatography on silica (50% EtOAc/hexane; yellow band from column) to give 6-methoxy-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)pyridin-3-amine (190 mg, 71.7% yield) as a yellow crystalline solid. 1H NMR (400 MHz, CDCl3) δ 12.06 (s, 1H); 9.68 (dd, J=7.82, 1.76 Hz, 1H); 8.99 (s, 1H); 8.44 (d, J=2.54 Hz, 1H); 8.28 (dd, J=4.69, 1.76 Hz, 1H) 8.34 (s, 1H); 8.05 (dd, J=8.90, 2.64 Hz, 1H); 6.88 (dd, J=7.82, 4.69 Hz, 1H); 6.77 (d, J=8.80 Hz, 1H); 5.86 (dd, J=10.37, 2.35 Hz, 1H); 4.16-4.25 (m, 1H); 3.95 (s, 3H); 3.82 (s, 1H); 1.98-2.24 (m, 3H); 1.61-1.89 (m, 3H). m/z (ESI, +ve) 404.0 (M+H)+.

Aufarbeitung

  1. customA blood-red solution was obtained
  2. customquenched with water (0.1 mL)
  3. extractionThe mixture was extracted into EtOAc from saturated aqueous NaHCO3
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica (50% EtOAc/hexane; yellow band from column)

Quellen und Nachweise

ORD-Eintrag
ord-569ea81b55d6403fb506da67a1c97d8b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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