Reacción #552540

Ecuación de reacción

pyridine

2-phenylamino-4-hydroxymethyl-6-cyclopropylpyrimidine

pyridine

thionyl bromide

sodium hydrogen carbonate

→

2-phenylamino-4-bromomethyl-6-cyclopropylpyrimidine

Disolventes

water

diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture is heated
2. 2
   Temperaturaunder reflux for 5 hours
3. 3
   TemperaturaAfter cooling to room temperature
4. 4
   OtroThe diethyl ether phase is separated off
5. 5
   Lavadowashed twice with 100 ml of water each time
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe solvent is evaporated
9. 9
   OtroThe brown oil which remains is purified by column chromatography over silica gel (toluene/chloroform/diethyl ether/petroleum ether (b.p. 50°-70° C.): 5/3/1/1)
10. 10
    OtroAfter the eluant mixture has been evaporated off
11. 11
    workup.ADDITIONthe yellow oil is diluted with diethyl ether/petroleum ether (b.p. 50°-70° C.)
12. 12
    Otrocrystallised at reduced temperature
13. 13
    Otro64% of the theoretical yield)

Procedimiento

15.6 g (75 mmol of thionyl bromide in 50 ml of diethyl ether are added dropwise within a period of half an hour, with stirring, to 12 g (50 mmol) of 2-phenylamino-4-hydroxymethyl-6-cyclopropylpyrimidine and 0.4 g (50 mmol) of pyridine in 350 ml of diethyl ether. After stirring for 2 hours at room temperature, a further 0.4 g (50 mmol) of pyridine are added and the mixture is heated under reflux for 5 hours. After cooling to room temperature, 200 ml of water are added and the pH is adjusted to 7 by the dropwise addition of 140 ml of saturated sodium hydrogen carbonate solution. The diethyl ether phase is separated off and then washed twice with 100 ml of water each time, dried over sodium sulfate and filtered, and the solvent is evaporated. The brown oil which remains is purified by column chromatography over silica gel (toluene/chloroform/diethyl ether/petroleum ether (b.p. 50°-70° C.): 5/3/1/1). After the eluant mixture has been evaporated off, the yellow oil is diluted with diethyl ether/petroleum ether (b.p. 50°-70° C.) and crystallised at reduced temperature. The yellow crystalline powder melts at 77.5°-79.5° C. Yield: 9.7 g (32 mmol; 64% of the theoretical yield).

Fuente