Ethyl Acetate → 2,4-Dichloro-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine

HRID 426258

Reaktionsgleichung

Reaktionsgleichung von HRID 426258
[H-].[Na+].[CH3:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[OH:12].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([CH:21]([CH3:23])[CH3:22])=[C:16]([Cl:24])[N:15]=1.C(OCC)(=O)C>CN(C=O)C>[Cl:13][C:14]1[N:15]=[C:16]([Cl:24])[C:17]([CH:21]([CH3:23])[CH3:22])=[C:18]([O:12][C:5]2[CH:6]=[C:7]([CH3:11])[CH:8]=[C:9]([CH3:10])[C:4]=2[CH3:3])[N:19]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 127692,3,5-TrimethylphenolHCID 24758Sodium hydrideHCID 2490092,4,6-Trichloro-5-isopropylpyrimidine

Produkt 1

HCID 591846652,4-Dichloro-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (60%, 59 mg, 1.44 mmol. 1.1 eq.) was added to 2,3,5-trimethyl-phenol (179 mg, 1.31 mmol) in DMF (2 mL). The mixture was stirred at room temperature for 15 minutes and then added to 2,4,6-trichloro-5-isopropyl-pyrimidine (296 mg, 1.31 mmol) in 1 mL DMF. The reaction was stirred at room temperature for 4 hours. Ethyl acetate was added and washed with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) to give white solid (400 mg, 94%). LC-MS shows 325.2 (M+1). 1H NMR (300 MHz, CDCl3): δ 6.94 (s, 1H), 6.63 (s, 1H), 3.61 (m, 1H), 2.32 (s, 6H), 2.02 (s, 3H), 1.42 (d, 6H).

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 4 hours
  2. washwashed with brine
  3. concentrationThe organic layer was concentrated down
  4. custompurified (silica gel, 0-50% EtOAC/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0e9d5a4705a9406daa7455443cbe0902
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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