Sodium hydride → 5-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine

HRID 2251498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251498
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH3:20])[CH:13]=2)=[N:7][CH:8]=1)[CH3:2].[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH3:20])[CH:13]=2)[CH2:28][C:27]2[CH:30]=[CH:31][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][CH:26]=2)=[N:7][CH:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 596433985-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]pyrimidin-2-amine

Produkt 1

HCID 690996425-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]pyrimidin-2-amine (0.83 g; 3.07 mmol) and 4-trifluoromethoxy benzyl bromide (1.18 g; 4.61 mmol) in dry DMF (6 ml) was treated under nitrogen with NaH (95% dispersion in oil; 0.12 g; 4.61 mmol) and the mixture heated at 60C for 1 hr. Cooled to rt and quenched with a saturated solution of ammonium chloride. Diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated. Purification by flash chromatography on silica gel using dichloromethane-hexane mixture (4:1) afforded 5-ethyl-N-[2-(4-methoxy-3-methylphenyl)ethyl]-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine (1.26 g; 82% yield).

Aufarbeitung

  1. customquenched with a saturated solution of ammonium chloride
  2. additionDiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-64b3724454e64488a758f728f33fa8d7
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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