Diisopropylethylamine → 6-Bromo-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928563노트

반응식

HRID 928563 반응식
[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.[N:27]1([CH2:32][CH2:33][O:34][CH2:35][CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:31][CH2:30][CH2:29][CH2:28]1>C1COCC1.O>[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([N:39]3[CH2:40][CH2:41][CH:36]([CH2:35][O:34][CH2:33][CH2:32][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:37][CH2:38]3)[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 895795126-Bromo-4-chloro-5-phenyl-thieno[2,3-d]pyrimidine

생성물 1

HCID 1177396476-Bromo-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine수율 66%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 6-bromo-4-chloro-5-phenyl-thieno[2,3-d]pyrimidine (0.820 g, 2.52 mmol) in THF (50 mL), was added diisopropylethylamine (0.65 mL, 3.78 mmol) and 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (0.801 g, 3.78 mmol) in one portion, and the reaction left to stir at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The reaction was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography using DCM: MeOH (0-25%) as eluent to afford the named product (0.828 g, 66%).

후처리

  1. waitthe reaction left
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe reaction was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography

출처 및 근거

ORD 기록
ord-1b9d70a88e734316a49f3e73505b9873
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

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