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

HRID 1250691

반응식

HRID 1250691 반응식
[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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidineHCID 222222883-Aminopropanamide hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-064543062e254504b9e2a0586f065070
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339089B2

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