Potassium Carbonate → 6-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-ol

HRID 28555

Reaktionsgleichung

Reaktionsgleichung von HRID 28555
C(O[C:4](=[O:17])[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])=O)C.Cl.[C:19]([NH2:22])(=[NH:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:6]2[N:21]=[C:19]([CH3:20])[NH:22][C:4](=[O:17])[CH:5]=2)[CH:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67170Acetamidine monohydrochlorideHCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

Produkt 1

HCID 1363418886-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-olAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-(5-chloro-2-methoxy-phenyl)-3-oxopropionic acid ethyl ester (0.9 g, 3.2 mmol), acetamidine hydrochloride (448 mg, 4.7 mmol) and potassium carbonate (1.3 g, 9.6 mmol) in ethanol (15 ml) was stirred at 100° C. in thick wall tube for 60 hours. After cooling to room temperature, the mixture was poured into ice cold water. The solid was collected by filtration, washed with water and ether and dried under vacuum to provide 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (530 mg, 68% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.32 (s, 3H, CH3), 3.85 (s, 3H, CH3), 6.77 (s, 1H, CH, Ar), 7.15 (d, 1H, J=8.8 Hz, Ar), 7.45 (dd, 1H, J=8.8 Hz, J=2.9 Hz, Ar), 7.90 (d, 1H, J=2.9 Hz, Ar), 12.42 (s, 1H, NH).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured into ice cold water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water and ether
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5314391f367944da93370148cb759c3c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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