Cesium carbonate → [4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-ol

HRID 31857

Reaktionsgleichung

Reaktionsgleichung von HRID 31857
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([CH2:19][OH:20])=[CH:7][N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[C:30](N)[N:29]=1>C1COCC1>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:9]1[C:8]([CH2:19][OH:20])=[CH:7][N:6]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 22142936{2-[(2-Aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl]methan-1-ol

Produkt 1

HCID 22142375[4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

{2-[(2-aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl}methan-1-ol was dissolved in 3 mL of anhydrous THF and 1.47 g (4.50 mmol) of anhydrous cesium carbonate was added. 2-chloro-5-nitro-6-aminopyridine (143 mg, 0.9 mmol) was added in one portion and the yellow suspension heated at 70° C. for 18 h. The reaction mixture was filtered, concentrated and the residue chromatographed (silica gel, 5% methanol/methylene chloride) to give [4-(2,4-dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-ol, 216 mg (53%), as a yellow solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe residue chromatographed (silica gel, 5% methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-b453eb9de7ad4eae8e3e303438f9931e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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