Reacción #552539

Ecuación de reacción

boron tribromide

2-anilino-4-methoxymethyl-6-cyclopropylpyrimidine

phenylguanidine

1-cyclopropyl-4-methoxy-1,3-butanedione

→

2-anilino-4-hydroxymethyl- 6-cyclopropylpyrimidine

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe cooling bath is then removed
2. 2
   workup.ADDITIONAfter the addition of 150 g of ice-water
3. 3
   Otrothe precipitated crude product
4. 4
   Filtraciónis filtered off
5. 5
   Otrorecrystallised from methanol using active carbon
6. 6
   Otromelt at 124°-126° C
7. 7
   Otro84.7% of the theoretical yield)

Procedimiento

5.9 g (23 mmol) of 2-anilino-4-methoxymethyl-6-cyclopropylpyrimidine, prepared from phenylguanidine and 1-cyclopropyl-4-methoxy-1,3-butanedione, are dissolved in 200 ml of dichloromethane and the solution is cooled to -68° C. 6.8 g (27 mmol) of boron tribromide are slowly added dropwise to the salmon-coloured solution within a period of half an hour, with vigorous stirring, and the cooling bath is then removed and stirring is continued for a further 2 hours at room temperature. After the addition of 150 g of ice-water, the precipitated crude product is filtered off and recrystallised from methanol using active carbon. The light-yellow crystals melt at 124°-126° C. Yield: 4.7 g (19.5 mmol; 84.7% of the theoretical yield).

Fuente