Reaktion #3264

Reaktionsgleichung

methylamine

4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester

triethylamine

→

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester

Ausbeute 81.0%

Lösungsmittel

hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen concentrated in vacuo
2. 2
   Sonstigepartitioned between chloroform and saturated aqueous sodium bicarbonate
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto provide a white solid
8. 8
   Filtrationfiltered

Vorschrift

To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40% aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to provide a white solid. The solid was suspended in hexane and filtered to provide 14.70 g (81%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester; mp 91°-93° C.

Quelle