Water → 4-(2-Furyl)-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

HRID 1865901

Reaktionsgleichung

Reaktionsgleichung von HRID 1865901
[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+].[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br)([O-:20])=[O:19].O>CN(C=O)C>[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[N:13]([CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=3)[N:14]=[CH:15][C:7]=12

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 220155004-(2-Furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

Produkt 1

HCID 220154894-(2-Furyl)-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (603 mg, 3 mmol) in DMF (3 mL) at 0° C. was treated with NaH (120 mg, 60%, 3 mmol), stirred for 20 min, treated with 3-nitrobenzyl bromide (648 mg, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography (EtOAc:Heptane, 1:1) to give the title compound as a cream solid (472 mg, 47%). A portion of the solid (70 mg) was suspended in MeOH, treated with HCl in dioxan (4-M, 1 mL), diluted with diethyl ether and filtered to give the hydrochloride salt of the title compound (79 mg, 100%) as a yellow solid.

Aufarbeitung

  1. stirringstirred at room temperature for 1 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography (EtOAc:Heptane, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1bbcb03ff2b24d80a48a2773019b90ea
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629349B2

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