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

HRID 50111

Reaktionsgleichung

Reaktionsgleichung von HRID 50111
[NH2:1][C:2](=[C:10]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.CNS(C)(=O)=O.C(O)(C)(C)C.[C:31]([N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])#[N:32].CC(C)([O-])C.[Na+]>>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH:16]([CH3:18])[CH3:17])[N:32]=[C:31]([N:33]([S:34]([CH3:37])(=[O:36])=[O:35])[CH3:38])[N:1]=2)=[CH:4][CH:5]=1

Komponenten

6

Edukt 5

HCID 6386tert-ButanolHCID 97632N-MethylmethanesulfonamideHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 23676156Sodium t-butoxideHCID 178500902HCID 178500902, Verbindung

Produkt 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylateAusbeute 68,1 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2.97 g (11.2 mmol) of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were introduced into 2.45 g (22.4 mmol) of N-methylmethanesulphonamide (MMSA) and 4.19 g (55.9 mmol) of tert-butanol together with 4.51 g (36.6 mmol) of N-cyano-N-methylmethanesulphonamide (CMMSA). 2.22 g (22.4 mmol) of sodium tert-butoxide were added to this suspension at room temperature in portions. An orange-coloured suspension was obtained. It was heated to 50° C. and stirred at 50° C. for 19.9 h. The suspension was poured onto 20 g of ice water, and the precipitate was filtered off and washed with water (2×5 ml). After drying in a high vacuum, 2.91 g of methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate were obtained in the form of a pale beige solid having a concentration of 76.4% (HPLC), which corresponds to a yield of 52.1%.

Aufarbeitung

  1. customAn orange-coloured suspension was obtained
  2. filtrationthe precipitate was filtered off
  3. washwashed with water (2×5 ml)
  4. customAfter drying in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b1b59e3fb9684bf5ab5277115677830f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710178B2

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