Sodium hydride → HCID 178518417, Verbindung

HRID 750806

Reaktionsgleichung

Reaktionsgleichung von HRID 750806
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].[H-].[Na+].CS([C:17]1[N:22]=[C:21]([OH:23])[C:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:19]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[N:18]=1)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][O:6][C:17]1[N:22]=[C:21]([OH:23])[C:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:19]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])[N:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 5228333,4-Difluorobenzyl alcoholHCID 178504853HCID 178504853, Verbindung

Produkt 1

HCID 178518417HCID 178518417, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a round bottom flask fitted with a magnetic stir bar and rubber septum was added 2 mL DMF, 3,4-difluorobenzyl alcohol (14 μl, 0.11 mmol) and sodium hydride (60% in oil, 4.5 mg, 0.12 mmol). The flask was flushed with nitrogen and 2-methylsulfonyl-4-hydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (from Step A) (43 mg, 0.1 mmol) in 500 μL DMF was added by syringe. After 1 h, the reaction was quenched with aqueous NH4Cl. A precipitate fell out of solution and it was filtered, washed with water and dried under reduced pressure. HPLC/MS: m/e=494 (M+); Rt=4.28 min; 1H-NMR 500 MHz (CDCl3): δ 5.39 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.09 (d, J=9 Hz, 2H), 7.15-7.22 (m, 4H), 7.22-7.28 (m, 1H), 7.41 (d, J=2 Hz, 1H).

Aufarbeitung

  1. customTo a round bottom flask fitted with a magnetic stir bar
  2. additionwas added by syringe
  3. customthe reaction was quenched with aqueous NH4Cl
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b29139e20e74d1ab0e9f4a651bd9c7f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405221B2

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