反应 #1702134

ord-b00902ac255049af941d30ae2a6494da

反应方程式

COc1cccc(CCCN)c1.Cl
3-(3-methoxyphenyl)propan-1-amine hydrochloride
Clc1ncc(Cl)c(Cl)n1
2,4,5-trichloropyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COc1cccc(CCCNc2nc(Cl)ncc2Cl)c1
desired product
收率 91.1%
COc1cccc(CCCNc2nc(Cl)ncc2Cl)c1
2,5-Dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine
收率 91.1%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The reaction was quenched with water
  2. 2
    workup.ADDITIONEtOAc was added
  3. 3
    其他the layers were separated
  4. 4
    萃取The aqueous layer was extracted with EtOAc twice
  5. 5
    洗涤The combined organic layers were washed with water and brine successively
  6. 6
    干燥dried (Na2SO4)
  7. 7
    过滤filtered
  8. 8
    浓缩concentrated (
  9. 9
    其他then triturated with cold EtOAc)

实验过程

To a solution of 3-(3-methoxyphenyl)propan-1-amine hydrochloride (2.00 g, 9.92 mmol) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.80 g, 34.7 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a light brown gel (2.82 g, 91%). LCMS for C14H16Cl2N3O (M+H)+: m/z=312.0, 314.0.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08765727B2uspto-grants-2014_07