2,4-Dichloropyrimidine → 6-(2-Chloropyrimidin-4-yl)-4-[6-tri-fluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

HRID 12277

Reaktionsgleichung

Reaktionsgleichung von HRID 12277
[O:1]=[C:2]1[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:6]=[C:5](B(O)O)[CH:4]=[C:3]1[C:19]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22]2[CH:32]=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:34]=[CH:35][C:21]=2[N:20]=1.[Cl:40][C:41]1[N:46]=[C:45](Cl)[CH:44]=[CH:43][N:42]=1.[F-].[K+]>C1COCC1.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]>[Cl:40][C:41]1[N:46]=[C:45]([C:5]2[CH:4]=[C:3]([C:19]3[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:30])[CH3:31])[C:22]4[CH:32]=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:34]=[CH:35][C:21]=4[N:20]=3)[C:2](=[O:1])[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[N:6]=2)[CH:44]=[CH:43][N:42]=1

Komponenten

6

Edukt 3

HCID 775312,4-DichloropyrimidineHCID 522689Potassium FluorideHCID 686805966-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid

Produkt 1

HCID 866116076-(2-Chloropyrimidin-4-yl)-4-[6-tri-fluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid, 2,4-di-chloropyrimidine, potassium fluoride and tris(dibenzylideneacetone)dipalladium(0) are dissolved in dry THF and degassed with argon for 10 minutes. Tri-tert-butyl-phosphonium tetrafluoroborate is added, and the reaction mixture is stirred at room temperature for 16 hours. LC-MS analysis shows complete conversion. The solvent is removed in a rotary evaporator, the residue is dissolved in DMF and the crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)). MS (ES+) m/z 653 (M+H).

Aufarbeitung

  1. customdegassed with argon for 10 minutes
  2. additionTri-tert-butyl-phosphonium tetrafluoroborate is added
  3. customThe solvent is removed in a rotary evaporator
  4. dissolutionthe residue is dissolved in DMF
  5. customthe crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

Quellen und Nachweise

ORD-Eintrag
ord-de6193c7d6a84e4199662d280a686708
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727989B2

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