Methyl pivaloylacetate → 6-tert-Butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one

HRID 253704

Reaktionsgleichung

Reaktionsgleichung von HRID 253704
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[NH:6].[O-]CC.[Na+].C[O:19][C:20](=O)[CH2:21][C:22](=O)[C:23]([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:23]([C:22]1[N:7]=[C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:12])([F:13])[F:1])[NH:6][C:20](=[O:19])[CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 99597Methyl pivaloylacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

Produkt 1

HCID 1361571906-tert-Butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-oneAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-trifluoromethylbenzamidine (1.12 g, 5 mmol), sodium ethoxide (1.02 g, 15 mmol) and 4,4-dimethyl-3-oxo-pentanoic acid methyl ester (0.80 mL, 5 mmol) in ethanol (50 mL) and was heated at reflux for 16 hours. The reaction was cooled, concentrated, diluted with water and acidified with 2 N hydrochloric acid. This solution was extracted with ethyl acetate, dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, methanol:dichloromethane (2:98)] provided the title compound (0.48 g, 32% yield) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) δ 12.8 (br s, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.78 (m, 2H), 7.71 (d, J=7.4 Hz, 1H), 6.24 (s, 1H), 1.20 (s, 9H) ppm; LC-MS 297.03 (M+H); Rt (Method A) 3.30 minutes.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additiondiluted with water
  6. extractionThis solution was extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification by flash chromatography [SiO2, methanol:dichloromethane (2:98)]

Quellen und Nachweise

ORD-Eintrag
ord-eea643965fc04e5f98dae4cbfd3e22de
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872129B2

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