Water → 6-Amino-N-benzyl-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxamide

HRID 8303

Reaktionsgleichung

Reaktionsgleichung von HRID 8303
[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.[CH2:16]([N:23]=[C:24]=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH2:12][C:10]1[N:9]=[C:8]2[N:13]([C:24]([NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])[N:14]=[CH:15][C:7]2=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:11]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 76639Benzyl isocyanateHCID 220155004-(2-Furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

Produkt 1

HCID 220155046-Amino-N-benzyl-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxamideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (210 mg, 1 mmol) in DMF (2 mL) was treated with benzyl isocyanate (123 μL, 1 mmol) and a catalytic amount of DMAP, stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by preparative HPLC (MeOH/H2O gradient) to give the title compound (80 mg, 24%) as a pale yellow solid. Method Q 4-(2-Furyl)-1-(4-indolymethyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (Example 65)

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative HPLC (MeOH/H2O gradient)

Quellen und Nachweise

ORD-Eintrag
ord-98c854739d60471ba63b9e181f7bfc00
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087754B2

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