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Diisopropylethylamine → {5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

HRID 1818923
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HRID 1818923 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH2:15])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[C:19]2[S:26][CH:25]=[CH:24][C:20]=2[N:21]=[CH:22][N:23]=1.CCN(C(C)C)C(C)C>CN(C)C=O.CCOC(C)=O.O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:18]2[C:19]3[S:26][CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 45117855tert-Butyl (5-(2-aminoethyl)thiazol-2-yl)carbamate2회

생성물 1

HCID 86603168{5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

시약·촉매·용매 3

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

[5-(2-Amino-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (compound 14.1; 20.5 mmol), compound 6.2 (0.94 equivalent) and DIEA (1.0 equivalent) was heated in N,N-dimethylformamide (“DMF”; 75 mL) at 90° C. for 1.5 hours. The reaction mixture was cooled and diluted with EtOAc and water. The organic layer was separated, washed with brine, dried, concentrated and purified by flash column chromatography on silica gel to provide {5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (compound 14.2) in 75% yield.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-7437534db748497f900b05175559c830
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07601725B2

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