Sodium Sulfide → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

HRID 1157542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157542
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[S-2].[Na+].[Na+]>O1CCOCC1.O>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 14804Sodium SulfideHCID 577372514-[2-(3-Nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

Produkt 1

HCID 577372234-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-[2-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine (809 mg, 1.98 mmol) in 1,4-dioxane (16 mL) was added sodium sulfide nonhydrate (1.05 g, 6 mmol) in water (4 mL). The mixture was heated at 90° C. for 5 h, allowed to cool to rt and concentrated in vacuo. The residue was diluted with EtOAc and water. The organic layer was separated and the aqueous layer is extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated to give a dark solid. The crude material was purified by silica gel chromatography (hexanes/EtOAc 30-50%) to afford the titled product (462 mg, 62% yield). 1H NMR (400 MHz, CDCl3): δ 3.75 (brs, 2H), 6.63 (d, 1H, J=5.3 Hz), 6.78 (m, 1H), 6.91 (m, 1H), 6.96-7.00 (m, 2H), 7.06 (m, 1H), 7.16 (m, 1H), 7.22-7.36 (m, 4H), 7.65 (m, 1H), 8.17 (d, 1H, J=5.3 Hz), 8.42 (m, 1H), 8.52 (m, 1H); ES-LC/MS m/z=379 [M+H]+.

Aufarbeitung

  1. temperatureto cool to rt
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with EtOAc and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer is extracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark solid
  10. customThe crude material was purified by silica gel chromatography (hexanes/EtOAc 30-50%)

Quellen und Nachweise

ORD-Eintrag
ord-6c3b8b4578d54be1830ff4c74c30ddad
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807673B2

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