3-Fluoro-4-morpholinoaniline → 2-((3,5-difluorophenoxy)methyl)-3-(3-fluoro-4-morpholinophenyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56245

반응식

HRID 56245 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].C[Al](C)C.C[O:20][C:21](=O)/[CH:22]=[C:23](\[NH:25][C:26](=O)[CH2:27][O:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=1)/[CH3:24]>C(Cl)Cl>[F:35][C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([F:36])[CH:32]=1)[O:28][CH2:27][C:26]1[N:5]([C:4]2[CH:6]=[CH:7][C:8]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[C:2]([F:1])[CH:3]=2)[C:21](=[O:20])[CH:22]=[C:23]([CH3:24])[N:25]=1

참가 물질

5

반응물 3

HCID 14853303-Fluoro-4-morpholinoanilineHCID 16682925TrimethylaluminumHCID 90023395(Z)-methyl-3-(2-(3,5-difluorophenoxy)acetamido)but-2-enoate

생성물 1

HCID 729492982-((3,5-difluorophenoxy)methyl)-3-(3-fluoro-4-morpholinophenyl)-6-methyl-pyrimidin-4(3H)-one수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-fluoro-4-morpholinoaniline (0.81 g, 4.13 mmol) in DCM (15 mL) was added trimethylaluminium (6.2 mL, 12.4 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-(3,5-difluorophenoxy)acetamido)but-2-enoate (1.18 g, 4.14 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred at rt for 12 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)=1:1) to give the title compound as a pale brown solid (1.08 g, 61%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringthe resulting mixture was stirred at rt for 12 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)=1:1)

출처 및 근거

ORD 기록
ord-f59bd13035e04d19accda90256fff2ea
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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