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

HRID 1725590

Reaktionsgleichung

Reaktionsgleichung von HRID 1725590
[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) δ12.8 (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-aec54b8393784005b76a4656b791942d
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491730B2

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