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Diisopropylethylamine → {4-[(2,5-Dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1819422
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HRID 1819422 반응식
[Cl:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CCO>[C:21]([O:20][C:19](=[O:25])[NH:18][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][NH:10][C:3]2[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)[CH2:17][CH2:16]1)([CH3:24])([CH3:22])[CH3:23]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 178453944HCID 178453944, 화합물

생성물 1

HCID 57885682{4-[(2,5-Dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester수율 99%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

To a solution of the above 5-chloro-2,4-dichloropyrimidine (73 mg, 0.4 mmol) in EtOH (2 mL) were added tert-butyl trans-4-aminomethylcyclohexylcarbamate (100 mg, 0.44 mmol) and DIPEA (77 μL, 0.44 mmol). The reaction mixture was heated at 40° C. for 1 h. The reaction mixture was concentrated in vacuo and the resulting residue was diluted with EtOAc. The solution was washed with brine. The aqueous layer was re-extracted with EtOAc (×2). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to yield 148 mg (99%) of {4-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resulting residue was diluted with EtOAc
  3. washThe solution was washed with brine
  4. extractionThe aqueous layer was re-extracted with EtOAc (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e511ebfdf1c741c681385cae4acb4522
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07601714B2

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