Acetonitrile → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 1160654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160654
[CH3:1][NH:2][S:3]([CH3:6])(=[O:5])=[O:4].C(#N)C.Cl[C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:14]([C:24]([O:26][CH3:27])=[O:25])=[C:13]([CH:28]([CH3:30])[CH3:29])[N:12]=1>O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[C:14]([C:24]([O:26][CH3:27])=[O:25])=[C:13]([CH:28]([CH3:30])[CH3:29])[N:12]=[C:11]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[N:16]=2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 97632N-MethylmethanesulfonamideHCID 11220571Methyl 2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate

Produkt 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
81.5 °C

Versuchsvorschrift

In a 25 mL-volume glass flask equipped with a stirrer, a thermometer and a reflux condenser were placed 546 mg (5 mmol.) of N-methylmethanesulfonamide, 551 mg (5 mmol.) of sodium t-pentoxide, 10 mL of acetonitrile, and 309 mg (1 mmol.) of 2-chloro-4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonylpyrimidine. The mixture was heated to 81-82° C. for 3 hours under refluxing, to carry out reaction. After the reaction was complete, the reaction mixture was cooled to room temperature. To the cooled mixture was added 10 mL of water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate portion was separated, and dried over anhydrous magnesium sulfate. The dried ethyl acetate portion was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (column: Wako Gel C-200, eluent: hexane/ethyl acetate (2:1, volume ratio)). There was obtained 339 mg of 4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-2-(N-methyl-N-methanesulfonylamino)pyrimidine. The yield was 89% (based on the amount of 2-chloro-4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonylpyrimidine).

Aufarbeitung

  1. customIn a 25 mL-volume glass flask equipped with a stirrer
  2. temperatureunder refluxing
  3. customreaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. extractionthe aqueous mixture was extracted with ethyl acetate
  6. customThe ethyl acetate portion was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe dried ethyl acetate portion was filtered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (column: Wako Gel C-200, eluent: hexane/ethyl acetate (2:1, volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-1127296202fa4dc39e4757f6a40c0575
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816528B2

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