Sodium hydride → A2A receptor antagonist 1

HRID 1865900

Reaktionsgleichung

Reaktionsgleichung von HRID 1865900
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10]([NH2:12])[N:9]=[C:8]2[NH:13][N:14]=[CH:15][C:7]=12.[H-].[Na+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br>CN(C=O)C>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][N:13]1[C:8]2=[N:9][C:10]([NH2:12])=[N:11][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[C:7]2[CH:15]=[N:14]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 220155004-(2-Furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

Produkt 1

HCID 9879687A2A receptor antagonist 1Ausbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (219 mg, 1 mmol) in DMF (2 mL) at 0° C. was treated with NaH (40 mg, 60%, 1 mmol), stirred for 20 min, treated with 2-fluorobenzyl bromide (120 μL, 1 mmol), stirred at room temperature for 1 h, quenched with water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (EtOAc:Heptane, 1:4) to give the title compound (250 mg, 76%) as a cream solid.

Aufarbeitung

  1. stirringstirred at room temperature for 1 h
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (EtOAc:Heptane, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-1196cb3c95834fa590604f4277f14ef5
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629349B2

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