Sodium hydride → 2,6-dichloro-N-(pyrimidin-4-yl)benzamide

HRID 449863

Reaktionsgleichung

Reaktionsgleichung von HRID 449863
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13](Cl)=[O:14]>CN(C=O)C>[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1)=[O:14]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 689584-AminopyrimidineHCID 783922,6-Dichlorobenzoyl chloride

Produkt 1

HCID 596183012,6-dichloro-N-(pyrimidin-4-yl)benzamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-aminopyrimidine (0.16 g, 1.72 mmol) was added to a cooled (0° C.) mixture of NaH (0.17 g, 4.25 mmol, 60% in mineral oil) in DMF (5 mL). The resulting mixture was stirred for 20 minutes under N2 at 0° C. and then 2,6-dichlorobenzoyl chloride (0.3 g, 1.43 mmol) was added dropwise. After one hour the reaction was poured into the ice-water (20 mL). The mixture was extracted with EtOAc (2×50 mL) and the combined organic extracts were concentrated under reduced pressue. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1) to afford the desired product (38 mg, yield 10%). 1HNMR: (DMSO-d6, 400 MHz): 611.73 (s, 1H), 8.91 (s, 1H), 8.74 (d, J=5.6 Hz, 1H), 8.17 (d, J=5.6 Hz, 1H), 7.55-7.47 (m, 3H). LCMS (ESI) m/z: 267.8 [M+H+]

Aufarbeitung

  1. temperaturea cooled
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. concentrationthe combined organic extracts were concentrated under reduced pressue
  4. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-920083cc0616484895e17cb24de5381a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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