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

HRID 928562노트

반응식

HRID 928562 반응식
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]([O:19][CH3:20])=[O:18])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(N(C(C)C)CC)(C)C.[N:30]1([CH2:35][CH2:36][O:37][CH2:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1.O>[C:11]1([C:10]2[C:3]3[C:2]([N:42]4[CH2:43][CH2:44][CH:39]([CH2:38][O:37][CH2:36][CH2:35][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:40][CH2:41]4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][C:9]=2[C:17]([O:19][CH3:20])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 89579551Methyl 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

생성물 1

HCID 89579481Methyl 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine-6-carboxylate수율 75.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.850 g, 2.80 mmol) in THF (50 mL), was added diisopropylethylamine (0.73 mL, 4.20 mmol) and 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (0.890 g, 4.20 mmol) in one portion, and the reaction left to stir at room temperature for 2 hours. 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 (1.012 g, 75%). m/z [M+H]+481; RT=3.03 min.

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-8aa1b08788be46e2a5bff4011e1f5254
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

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