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

HRID 1250671노트

반응식

HRID 1250671 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.C(N(CC)CC)C.Cl.[CH2:21]([NH2:30])/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:30][CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6444486Cinnamylamine hydrochloride, (E)-HCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidine

생성물 1

HCID 183264422-Chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine수율 54%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 10 ml of a solution of 438 mg (2.0 mmol) of 2,4-dichloro-7-metylthieno[3,2-d]pyrimidine and 445 mg (4.4 mmol) of triethylamine in DMF was added 339 mg (2.0 mmol) of trans-cinnamylamine hydrochloride under ice cooling. The reaction mixture was stirred at the same temperature for one hour and then allowed to resume room temperature, followed by stirring for further 2 hours. 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=1/4) to give 341 mg (yield: 54.0%) of the title compound.

후처리

  1. customto resume room temperature
  2. stirringby stirring for further 2 hours
  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=1/4)

출처 및 근거

ORD 기록
ord-0647b7b1a30c4fd8b9cb64434c290bb1
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339089B2

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