Methyl iodide → 6-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 469297

Reaktionsgleichung

Reaktionsgleichung von HRID 469297
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[NH:16][C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1.I[CH3:24]>CN(C=O)C>[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[N:16]([CH3:24])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Produkt 1

HCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.35 g (8.0 mmol) sodium hydride (55%, suspension in mineral oil) were added to 2.2 g (7.6 mmol) of 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL N,N′-dimethylformamide. The reaction mixture was stirred for 30 min at RT. Then 0.95 mL (15.0 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. The reaction mixture was combined with ice water, the aqueous phase was extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and concentrated to dryness by rotary evaporation. The residue was triturated with diethyl ether, suction filtered and dried.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 h at RT
  2. extractionthe aqueous phase was extracted several times with EtOAc
  3. customThe combined organic phases were dried on sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness by rotary evaporation
  6. customThe residue was triturated with diethyl ether, suction
  7. filtrationfiltered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3356c125830d411c8dd00e039d488881
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629137B2

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