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

HRID 56273ノート

反応式

HRID 56273 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 7237O-Xylene溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-2a99ca492f3e4809b414e5c4b7aa3abf
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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