Potassium Carbonate → 2-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

HRID 1958456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958456
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[O:18][CH3:19].C([O-])([O-])=O.[K+].[K+].Cl[C:27]1[N:32]=[C:31]([Cl:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][N:28]=1>O1CCOCC1>[Cl:33][C:31]1[C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][N:28]=[C:27]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][C:3]=2[O:18][CH3:19])[N:32]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 58200992Benzyl 4-amino-3-methoxybenzoate

Produkt 1

HCID 582010032-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Benzyl 4-amino-3-methoxybenzoate (1.92 g, 6.8 mmol) and K2CO3 (2.38 g, 17 mmol) are suspended in 4 mL dioxane and then mixed with 2,4-dichloro-5-trifluoromethylpyrimidine (1.48 mL, 6.8 mmol). The suspension is then refluxed for 100 min with stirring in the oil bath (approx. 130° C.). Once the reaction has ended the reaction mixture is filtered, the filtrate is concentrated by rotary evaporation and purified by normal-phase column chromatography. The product-containing fractions of A-3a (HPLC-MS: tRet.=1.94 min; MS (m-H)−=436) are combined and concentrated by rotary evaporation.

Aufarbeitung

  1. temperatureThe suspension is then refluxed for 100 min
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated by rotary evaporation
  4. custompurified by normal-phase column chromatography
  5. customThe product-containing fractions of A-3a (HPLC-MS: tRet.=1.94 min; MS (m-H)−=436)
  6. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-2b5f64ccd23f46e18518e0d88d76e75d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410126B2

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