Methyl acetoacetate → 4(3H)-Pyrimidinone, 6-methyl-2-[2-(trifluoromethyl)phenyl]-

HRID 253701

Reaktionsgleichung

Reaktionsgleichung von HRID 253701
[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:18](OC)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C(O)C>[CH3:22][C:20]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:18](=[O:23])[CH:19]=1

Komponenten

5

Edukt 3

HCID 7757Methyl acetoacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

Produkt 1

HCID 1358508354(3H)-Pyrimidinone, 6-methyl-2-[2-(trifluoromethyl)phenyl]-Ausbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-trifluoromethyl-benzamidine (2.13 g, 4 mmol) and sodium ethoxide (0.83 g, 12 mmol) in ethanol (20 mL) was treated with methyl acetoacetate (0.44 mL, 4 mmol) and heated at for 24 hours. The reaction was cooled, concentrated, diluted with water and acidified with 2 N hydrochloric acid. The resulting solution was extracted with ethyl acetate, dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, methanol:dichloromethane (3:97)] provided the title compound (0.51 g, 50% yield) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) δ 12.7 (br s, 1H), 7.9 (m, 1H), 7.8 (m, 2H), 7.7 (m, 1H), 6.3 (s, 1H), 2.21 (s, 3H) ppm; MS (FIA) 255.0 (M+H); Rt (Method A) 2.578 minutes.

Aufarbeitung

  1. temperatureheated at for 24 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additiondiluted with water
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography [SiO2, methanol:dichloromethane (3:97)]

Quellen und Nachweise

ORD-Eintrag
ord-498c478e0ede464c8788cf90134de9c7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872129B2

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