Reacción #79782

Ecuación de reacción

cyclopentanesulphonyl chloride

Sodium hydride

5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

→

7-cyclopentanesulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Disolventes

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   Otroevaporated under vacuum
3. 3
   OtroThe residue was triturated with water
4. 4
   Filtraciónfiltered
5. 5
   Otroto give a solid which
6. 6
   Lavadowas washed well with water
7. 7
   workup.STIRRINGstirred with ethyl acetate
8. 8
   Filtraciónthen filtered
9. 9
   OtroThe filtrate was purified by flash column chromatography on silica
10. 10
    OtroAppropriate fractions were collected
11. 11
    Otroevaporated

Procedimiento

Sodium hydride (0.132 g of a 60% dispersion in mineral oil) was added to a solution of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.0 g) in dry dimethylformamide (30 ml) with stirring under nitrogen. The mixture was stirred for 30 minutes and then cyclopentanesulphonyl chloride (0.558 g, prepared as described in J.O.C.1952, 17, 1529-1533) in dry dimethylformamide (5 ml) was added dropwise. The mixture was allowed to stand for 72 hours and then evaporated under vacuum. The residue was triturated with water and filtered to give a solid which was washed well with water, then stirred with ethyl acetate then filtered. The filtrate was purified by flash column chromatography on silica using ethyl acetate as the mobile phase. Appropriate fractions were collected and evaporated to give 7-cyclopentanesulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 188-188.5° C.

Fuente