Reaktion #577419

Reaktionsgleichung

water

3-amino-5-methylpyrazole

4,6-dichloro-2-(methylthio)pyrimidine

diisopropylamine

→

title compound

Ausbeute 67.5%

6-Chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylthio)pyrimidin-4-amine

Ausbeute 67.5%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter which time all of the starting material had reacted (by LC/MS analysis)
2. 2
   TemperaturThe mixture was cooled to ambient and
3. 3
   FiltrationThe precipitate was filtered
4. 4
   FiltrationThe solid was again filtered and re-slurried in methanol (100 ml)
5. 5
   Sonstigedried on the sinter
6. 6
   Sonstigefurther dried under vacuum

Vorschrift

To a stirred solution of 4,6-dichloro-2-(methylthio)pyrimidine (25 g, 0.128 mol) in DMF (100 ml) was added diisopropylamine (19.8 g, 0.154 mol) followed by 3-amino-5-methylpyrazole (13.7 g, 0.154 mol) portionwise over 10 minutes. The solution was heated to 50° C. for 16 hours, after which time all of the starting material had reacted (by LC/MS analysis). The mixture was cooled to ambient and poured into water (250 ml). The precipitate was filtered and the wet solid slurried in diethyl ether (300 ml). The solid was again filtered and re-slurried in methanol (100 ml). The filtered product was air dried on the sinter, then further dried under vacuum. This afford the title compound as an off-white solid (22.1 g, 66% yield). 1H NMR (d6-DMSO) δ 2.22 (3H, s, CH3), 3.31 (3H, s, CH3), 6.00-7.50 (2H, br, CH), 10.17 (1H, s, NH), 12.10 (1H, s, NH); MS ES+256.08, ES−254.25.

Quelle