三乙胺 → 2-Chloro-4-(2-carbamoylethylamino)-7-methylthieno[3,2-d]pyrimidine

HRID 1250691

反应方程式

HRID 1250691 反应方程式
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.Cl.[NH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[O:18].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:14][CH2:15][CH2:16][C:17](=[O:18])[NH2:19])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

参与物

5

反应物 3

HCID 8471三乙胺HCID 71470642,4-二氯-7-甲基噻吩并[3,2-D]嘧啶HCID 22222288BETA-丙胺酰胺盐酸盐

产物 1

HCID 183264112-Chloro-4-(2-carbamoylethylamino)-7-methylthieno[3,2-d]pyrimidine收率 79.8%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
0 °C

实验过程

In 10 ml of DMF, 1.0 g (4.9 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine was dissolved, and then 668 mg (5.37 mmol) of β-alanineamide hydrochloride and 1.09 g (10.7 mmol) of triethylamine were added thereto under ice cooling. The reaction solution was stirred at 0° C. for one hour and then allowed to resume room temperature, followed by stirring for further 1 hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8) to give 1.05 g (yield: 79.8%) of the title compound.

后处理

  1. customto resume room temperature
  2. stirringby stirring for further 1 hour
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  5. washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8)

来源与证据

ORD记录
ord-064543062e254504b9e2a0586f065070
来源数据集
uspto-grants-2002_01
专利号
US06339089B2

关联笔记

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