3-Fluoro-4-[2-(4-morpholinyl)ethoxy]phenylamine → 3-(3-fluoro-4-(2-morpholinoethoxy)phenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56262노트

반응식

HRID 56262 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[NH2:5].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]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]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:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

참가 물질

5

반응물 3

HCID 121254503-Fluoro-4-[2-(4-morpholinyl)ethoxy]phenylamineHCID 16682925TrimethylaluminumHCID 90022556Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate

생성물 1

HCID 900236073-(3-fluoro-4-(2-morpholinoethoxy)phenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one수율 30.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-fluoro-4-(2-morpholinoethoxy)aniline (0.33 g, 1.37 mmol) in DCM (20 mL) was added trimethylaluminium (2.7 mL, 5.40 mmol, 2 M in toluene) 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. The mixture was quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=30:1) to give the title compound as a pale yellow solid (0.19 g, 30%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringthe resulting mixture was stirred at rt for 24 h
  2. customThe mixture was quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×2)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=30:1)

출처 및 근거

ORD 기록
ord-5e295c81afdc4f78b3526683b28316cf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

반응 노트

불러오는 중…