Réaction #86409

Équation de réaction

Water

2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene

N-(2-nitro-phenyl)-N′-pyridin-3-ylmethyl-pyrimidine-4,6-diamine

NaH

→

title compound

Rendement 32.0%

3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-[6-(2-nitro-phenylamino)pyrimidin-4-yl]1-pyridin-3-ylmethyl-urea

Rendement 32.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 2 hours
2. 2
   Autreto quench
3. 3
   Autrethe reaction
4. 4
   ConcentrationThe mixture was concentrated
5. 5
   Autrethe residue was purified by flash chromatography on silica

Mode opératoire

To a solution of N-(2-nitro-phenyl)-N′-pyridin-3-ylmethyl-pyrimidine-4,6-diamine (150 g, 0.467 mmol) in THF (15 mL) was added NaH (60%, 48 g, 1.2 mmol) at 0° C., and the mixture was stirred for 30 minutes at room temperature. A solution of 2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene (procedure 2A, steps a-d; 180 g, 0.73 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 2 hours. Water (2 mL) was added to quench the reaction. The mixture was concentrated, and the residue was purified by flash chromatography on silica to obtain the title compound (85 mg, yield: 32%). MS (ESI): 570 [M+H]+.

Source