Réaction #1565207

Équation de réaction

5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro [5.5]undecan-9-yl)pyrimidine-2,4-diamine

2-cyanoacetic acid

O-(7-aza-1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

N,N-diethylethanamine

→

title compound

Rendement 15.6%

3-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile

Rendement 15.6%

Solvants

DCM

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated in vacuo
2. 2
   AutreThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1)

Mode opératoire

To a suspension 5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro [5.5]undecan-9-yl)pyrimidine-2,4-diamine (165 mg, 0.42 mmol) and 2-cyanoacetic acid (107.18 mg, 1.26 mmol) in a mixture of DCM and N,N-dimethylformamide (8 mL/2 mL) were added O-(7-aza-1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (85.75 mg, 0.63 mmol) and N,N-diethylethanamine (127.50 mg, 1.26 mmol). The mixture was stirred at rt overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1) to give the title compound as a yellow solid (30 mg, 15.54%).

Source