2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(4-(bis(2-propoxyethyl)amino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one

HRID 56176노트

반응식

HRID 56176 반응식
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15].C[Al](C)C.[NH:26](/[C:30](/[CH3:36])=[CH:31]\[C:32](OC)=[O:33])[C:27]([CH3:29])=O>C(Cl)Cl>[CH2:13]([O:12][CH2:11][CH2:10][N:9]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH3:21])[C:3]1[CH:4]=[CH:5][C:6]([N:8]2[C:32](=[O:33])[CH:31]=[C:30]([CH3:36])[N:26]=[C:27]2[CH3:29])=[CH:7][C:2]=1[F:1])[CH2:14][CH3:15]

참가 물질

5

반응물 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 1179660932-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine

생성물 1

HCID 729500013-(4-(bis(2-propoxyethyl)amino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-fluoro-N1,N1-bis(2-propoxyethyl)benzene-1,4-diamine (0.50 g, 1.68 mmol) in CH2Cl2 (10 mL) was added trimethylaluminum (3.4 mL, 6.8 mmol, 2 M in toluene) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.32 g, 2.02 mmol) in CH2Cl2 (2 mL). The reaction mixture was stirred at rt for 72 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as pale yellow oil (0.53 g, 78%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringThe reaction mixture was stirred at rt for 72 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

출처 및 근거

ORD 기록
ord-7c3b65d676664db99dc9b02695df5e4e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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