2-Nitroaniline → N-(2-Nitro-phenyl)-N'-pyridin-3-ylmethyl-pyrimidine-4,6-diamine

HRID 58130

Reaktionsgleichung

Reaktionsgleichung von HRID 58130
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25])([O-:18])=[O:17].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:5]=[CH:6][N:7]=1)([O-:18])=[O:17]

Komponenten

7

Edukt 4

HCID 69462-NitroanilineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 534102806-Chloro-N-(3-pyridinylmethyl)-4-pyrimidinamine

Produkt 1

HCID 118024538N-(2-Nitro-phenyl)-N'-pyridin-3-ylmethyl-pyrimidine-4,6-diamineAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A degassed mixture of (6-chloro-pyrimidin-4-yl)-pyridin-3-ylmethyl-amine (300 g, 1.36 mmol), 2-nitro-phenylamine (188 g, 1.36 mmol), Pd2(dba)3 (128 g, 0.14 mmol), Xantphos (161 g, 0.28 mmol) and Cs2CO3 (913 g, 2.8 mmol) in toluene (10 mL) was heated at 100° C. for 4 hours. The reaction was concentrated, and the residue was purified by flash chromatography on silica to obtain the title compound (150 mg, yield: 34%). MS (ESI): 323 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-45ef8b5d42ca4fddb9c93ddaed8e35ba
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

Verknüpfte Notizen

Wird geladen…