Реакция #86409

Уравнение реакции

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

Выход 32.0%

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

Выход 32.0%

Растворители

THF

Условия реакции

Обработка

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

Методика

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]+.

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