Dimethylformamide → 4-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidine

HRID 28556

Reaktionsgleichung

Reaktionsgleichung von HRID 28556
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2[N:13]=[C:12]([CH3:14])[NH:11][C:10](=O)[CH:9]=2)[CH:7]=1.CN(C)C=O.C(Cl)(=O)C([Cl:26])=O>ClCCl.O1CCOCC1>[Cl:26][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[N:13]=[C:12]([CH3:14])[N:11]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1363418886-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-ol

Produkt 1

HCID 656453264-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (520 mg, 2.1 mmol) in dichloromethane (20 ml) and 1,4-dioxane (20 ml) was added N,N-dimethylformamide (0.2 ml) followed by a solution of oxalyl chloride in dichloromethane (2 M, 4.2 ml). After stirring for 1 hour, the mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml). The organic phase was dried over magnesium sulfate and concentrated under vacuum to give 4-chloro-6-(5-chloro-2-methoxy-phenyl)-2-methyl-pyrimidine (530 mg, 94% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.67 (s, 3H, CH3), 3.91 (s, 3H, CH3), 7.26 (d, 1H, J=9.2 Hz, Ar), 7.59 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.95 (s, 1H, Ar), 7.96 (d, 1H, J=2.9 Hz, Ar).

Aufarbeitung

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4749b9b34d4d42a3a1c43ccca0c7b463
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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