Dimethylformamide → HCID 57990384, Verbindung

HRID 2381745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381745
[CH2:1]([NH:8][C:9]1[C:10]2[C:18](I)=[CH:17][N:16]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:11]=2[N:12]=[C:13]([Cl:15])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][N:31](C=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2]>[CH2:1]([NH:8][C:9]1[C:10]2[C:18]([C:30]#[N:31])=[CH:17][N:16]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:11]=2[N:12]=[C:13]([Cl:15])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 57990349HCID 57990349, Verbindung

Produkt 1

HCID 57990384HCID 57990384, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of N-benzyl-2-chloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (386 mg, 0.716 mmol), Pd2 dba3 (40 mg, 0.043 mmol) and dppf (80 mg, 0.14 mmol) in DMF (6 mL) was degassed with argon before being charged with Zn(CN)2 (100 mg, 0.555 mmol). The mixture was stirred at 70° C. for 20 h. DMF was removed in vacuo. The residue was purified by HPLC to give 4-(benzylamino)-2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (54 mg).

Aufarbeitung

  1. customDMF was removed in vacuo
  2. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8e183fef26044d168b20ccb5b3832666
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258144B2

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