반응 #86406

반응 방정식

Water

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

N-methyl-N′-(2-nitro-phenyl)-pyrimidine-4,6-diamine

NaH

→

title compound

수율 18.0%

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

수율 18.0%

용매

EtOAc

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 2 hours
2. 2
   기타to quench
3. 3
   기타the reaction
4. 4
   농축The mixture was concentrated
5. 5
   기타the residue was purified by flash chromatography on silica eluting with DCM

실험 절차

To a solution of N-methyl-N′-(2-nitro-phenyl)-pyrimidine-4,6-diamine (150 g, 0.61 mmol) in THF (15 mL) was added NaH (60%, 60 g, 1.5 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 (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 eluting with DCM:EtOAc=6:1-1:1 to obtain the title compound (54 mg, yield: 18%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 3.38 (s, 3H), 3.93 (s, 6H), 6.75 (s, 1H), 6.91 (s, 1H), 7.34 (t, 1H), 7.72 (t, 1H), 7.79 (d, 1H), 8.01 (d, 1H), 8.38 (s, 1H), 9.99 (s, 1H), 11.78 (s, 1H); MS (ESI): 493 [M+H]+.

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