Reacción #2292785

Ecuación de reacción

2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile

tert-butyl (S)-4-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-methylpiperazine-1-carboxylate

Triethylamine

→

title compound

Rendimiento 90.0%

tert-Butyl (S)-4-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-methylpiperazine-1-carboxylate

Rendimiento 90.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Otrothe mixture was partitioned between saturated NaHCO3 and ethyl acetate
3. 3
   ExtracciónThe aqueous layer was extracted with ethyl acetate
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe crude product was purified by column chromatography (SiO2, 20-100% EtOAc/heptane gradient)
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

To a 250 mL round-bottom flask were added 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (0.821 g, 4.87 mmol) and tert-butyl (S)-4-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-methylpiperazine-1-carboxylate (1.40 g, 3.75 mmol) in DMSO (15 mL). Triethylamine (2.1 mL, 15 mmol) was added to the mixture, which was then heated to 85° C. for 2 hours. After cooling, the mixture was partitioned between saturated NaHCO3 and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (SiO2, 20-100% EtOAc/heptane gradient). The product-containing fractions were combined and then concentrated in vacuo to give the title compound as light-yellow oil (1.7 g, 90%). ESI-MS m/z [M+H]+ calc'd for C26H35N9O2, 506. found 506.

Fuente