Reacción #2257335

Ecuación de reacción

2,4,5-trichloropyrrolo[2,1-f][1,2,4]triazine

DIPEA

pyridin-2-ylmethanamine

→

2,5-dichloro-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Rendimiento 57.1%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe reaction mixture was washed with water
2. 2
   Otrothe organic layer was separated
3. 3
   Secadodried over anhydrous Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   Otroto give a brown solid
7. 7
   OtroThe residue was purified by column chromatography

Procedimiento

To a stirred solution of 2,4,5-trichloropyrrolo[2,1-f][1,2,4]triazine (0.530 g, 2.38 mmol) in CH2Cl2 (20 mL) was added DIPEA (0.832 mL, 4.76 mmol) and pyridin-2-ylmethanamine (0.283 g, 2.62 mmol) and the contents were stirred for 10 min at room temperature. The reaction mixture was washed with water and the organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a brown solid. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 20% EtOAc/hexanes) to give 2,5-dichloro-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.400 g, 57.0%) as an off-white solid. LCMS Condition B-12: retention time 2.20, [M+1]=294.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.87 (d, J=5.7 Hz, 2H), 6.81 (d, J=2.8 Hz, 1H), 7.32 (t, J=1.6 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.81 (d, J=2.8 Hz, 1H), 7.83 (t, J=1.6 Hz, 1H), 8.48 (t, J=5.2 Hz, 1H), 8.57 (d, J=1.2 Hz, 1H).

Fuente