Water → 3-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2-((3-fluorophenoxy)methyl)-6-methylpyrimidin-4(3H)-one

HRID 56263노트

반응식

HRID 56263 반응식
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C[Al](C)C.C[O:23][C:24](=O)/[CH:25]=[C:26](\[NH:28][C:29](=O)[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)/[CH3:27].O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:24](=[O:23])[CH:25]=[C:26]([CH3:27])[N:28]=[C:29]2[CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=2)[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

참가 물질

6

반응물 4

HCID 962WaterHCID 16682925TrimethylaluminumHCID 176096902-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamineHCID 90022556Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate

생성물 1

HCID 900314133-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2-((3-fluorophenoxy)methyl)-6-methylpyrimidin-4(3H)-one수율 79.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamine (0.33 g, 1.38 mmol) in DCM (20 mL) was added trimethylaluminium (2.1 mL, 4.2 mmol, 2 M in toluene) slowly and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-(3-fluorophenoxy)acetamido)but-2-enoate (0.37 g, 1.38 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred at rt for 24 h. 50 mL of water was then added to the mixture slowly and the mixture was extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as a pale yellow solid (0.5 g, 79%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringthe resulting mixture was stirred at rt for 24 h
  2. extractionthe mixture was extracted with CH2Cl2 (50 mL×2)
  3. washThe combined organic phases were washed with brine (100 mL×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc)

출처 및 근거

ORD 기록
ord-5039eba7e6064f93b17f0bea4b9ad88e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

반응 노트

불러오는 중…