Reaktion #58356

Reaktionsgleichung

H2O

Et3N

4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde

2,6-difluoroaniline

→

4-chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Ausbeute 76.2%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 24 h
3. 3
   Sonstigethe layers were separated
4. 4
   SonstigeThe organic layer was evaporated
5. 5
   Sonstigethe crude product was recrystallized from 200 mL of a methanol

Vorschrift

To a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (11.1 grams(hereinafter “g”), 50 millimoles (hereinafter “mmol”)) in CHCl3 (100 milliliters (hereinafter “mL”)) was added 2,6-difluoroaniline (8.07 mL, 75 mmol, 1.5 equivalents (hereinafter “eq”)) followed by Et3N (10.43 mL, 75 mmol, 1.5 eq). The reaction mixture turned yellow and was heated to reflux for 24 h, H2O (50 mL) was added and the layers were separated. The organic layer was evaporated and the crude product was recrystallized from 200 mL of a methanol: H2O mixture (2:1) to give 12.03 g (76%) of pure 4-chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 2.21 (s, 3H), 6.91 (m, 2H), 7.24 (m, 1H), 10.29 (s, 1H), 10.35 (br s, 1H). LC MS (m/e)=316 (MH+).

Quelle