Potassium Phosphate, Tribasic → 6-(2-Cyclopropylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

HRID 12296

Reaktionsgleichung

Reaktionsgleichung von HRID 12296
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([C:23]3[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]4[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=4[N:24]=3)[C:11](=[O:22])[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1.[CH:40]1(B(O)O)[CH2:42][CH2:41]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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.Cl[Pd]Cl.[Fe+2]>[CH:40]1([C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[C:10]([C:23]4[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]5[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=5[N:24]=4)[C:11](=[O:22])[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=3)[CH:5]=[CH:4][N:3]=2)[CH2:42][CH2:41]1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 866116106-(2-chloropyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Produkt 1

HCID 686798776-(2-Cyclopropylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

100 mg of 6-(2-chloropyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 29.2 mg of cyclopropylboronic acid and 138 mg of potassium phosphate are dissolved in 1 ml of toluene and 0.05 ml of water and, under an argon atmosphere, 17 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (1:1 complex with CH2Cl2) are added. The mixture is stirred at 100° C. for 9 h. After cooling to room temperature, it is diluted with 15 ml of water and extracted several times with ethyl acetate, and the combined organic phases are extracted once more with saturated sodium chloride solution and dried using a Varian Chem Elut CE 1005 cartridge. The crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH)).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted several times with ethyl acetate
  3. extractionthe combined organic phases are extracted once more with saturated sodium chloride solution
  4. customdried
  5. customThe crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH))

Quellen und Nachweise

ORD-Eintrag
ord-75bad0bdb18843a0926daf2d162608bf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727989B2

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