Water → 3-(3-fluoro-4-morpholinophenyl)-2-(((5-fluoropyridin-3-yl)oxy)methyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56273노트

반응식

HRID 56273 반응식
[F:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C:10]([NH2:12])=O)[CH:5]=[N:6][CH:7]=1.[F:13][C:14]1[CH:15]=[C:16]([NH:26][C:27](=[O:32])[CH2:28][C:29](=O)[CH3:30])[CH:17]=[CH:18][C:19]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CCOC(C)=O.O>C1(C)C(C)=CC=CC=1.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.C([O-])(C)C.[Ti+4]>[F:13][C:14]1[CH:15]=[C:16]([N:26]2[C:27](=[O:32])[CH:28]=[C:29]([CH3:30])[N:12]=[C:10]2[CH2:9][O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:17]=[CH:18][C:19]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 900226812-((5-Fluoropyridin-3-yl)oxy)acetamideHCID 90023295N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

생성물 1

HCID 900516953-(3-fluoro-4-morpholinophenyl)-2-(((5-fluoropyridin-3-yl)oxy)methyl)-6-methyl-pyrimidin-4(3H)-one수율 27%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 7237O-Xylene용매

실험 절차

To a mixture of 2-((5-fluoropyridin-3-yl)oxy)acetamide (200 mg, 1.18 mmol) and N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (330 mg, 1.18 mmol) in xylene (10 mL) was added titanium tetraisopropanolate (2.7 mg, 9.5 mmol) and the mixture was refluxed for 50 h. The mixture was cooled to rt and 60 mL of EtOAc and 10 mL of water were added. The resulting mixture was filtered and the filtrate was 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 yellow solid (130 mg, 27%). The compound was characterized by the following spectroscopic data:

후처리

  1. temperaturethe mixture was refluxed for 50 h
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

출처 및 근거

ORD 기록
ord-2a99ca492f3e4809b414e5c4b7aa3abf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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