天然气 → 5-(4-Methylphenyl)-4,6-dichloro-2-(2-thienyl)pyrimidine

HRID 2318

反应方程式

HRID 2318 反应方程式
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.CCCCCC.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([Cl:31])=[N:26][CH:27]=[N:28][C:29]=2[Cl:30])=[CH:20][CH:19]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C>O1CCCC1.O.C(O)(=O)C>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:29]([Cl:30])=[N:28][C:27]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:26][C:25]=2[Cl:31])=[CH:22][CH:23]=1

参与物

9

反应物 5

HCID 297天然气HCID 67752,3-二氯-5,6-二氰基苯醌(DDQ)HCID 8030噻吩HCID 219795544,6-DICHLORO-5-P-TOLYLPYRIMIDINEHCID 178418244HCID 178418244，化合物

产物 1

HCID 196895045-(4-Methylphenyl)-4,6-dichloro-2-(2-thienyl)pyrimidine收率 49.1%

试剂、催化剂与溶剂 3

HCID 176醋酸溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂3 次

反应条件

温度
0 °C

实验过程

To a solution of thiophene (1.69 g) in anhydrous tetrahydrofuran (20 ml) is added dropwise a 1.6M n-butyl lithium/n-hexane solution (11.4 ml) at 0° C. under argon atmosphere over a period of 30 minutes. To the mixture is added dropwise and gradually a solution of 5-(4-methylphenyl)-4,6-dichloropyrimidine (4.0 g) in anhydrous tetrahydrofuran (5 ml) at -60° C. The mixture is warmed to 0° C., and stirred for 1.5 hour. After the reaction is complete, to the mixture are added acetic acid (1.5 g) and water (0.25 g), and further added thereto a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.70 g) in tetrahydrofuran (5 ml), and the mixture is stirred at 0° C. for one hour. The mixture is treated with an active charcoal, and extracted with a mixture of ethyl acetate and aqueous citric acid solution. The extract is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=50:1) to give 5-(4-methylphenyl)-4,6-dichloro-2-(2-thienyl)pyrimidine (2.64 g) as powder.

后处理

  1. additionTo the mixture is added dropwise
  2. customat -60° C
  3. additionfurther added
  4. extractionextracted with a mixture of ethyl acetate and aqueous citric acid solution
  5. washThe extract is washed
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=50:1)

来源与证据

ORD记录
ord-1ce4869becc14147b48b50fb8a727e75
来源数据集
uspto-grants-1998_03
专利号
US05728706

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