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Toluene → 3-(4-(dihexylamino)-3-fluorophenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56279
ノート
印刷プレビュー

反応式

HRID 56279 の反応式
[CH2:1]([N:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:20])[CH2:16][C:17](=O)[CH3:18])=[CH:10][C:9]=1[F:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:28][C:29]1[CH:30]=[C:31]([CH:37]=[CH:38][CH:39]=1)[O:32][CH2:33][C:34]([NH2:36])=O.C1(C)C=CC=CC=1.[NH4+].[Cl-]>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]>[CH2:1]([N:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:15](=[O:20])[CH:16]=[C:17]([CH3:18])[N:36]=[C:34]2[CH2:33][O:32][C:31]2[CH:37]=[CH:38][CH:39]=[C:29]([F:28])[CH:30]=2)=[CH:10][C:9]=1[F:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 189381052-(3-Fluorophenoxy)acetamideHCID 90023627N-(4-(dihexylamino)-3-fluorophenyl)-3-oxobutanamide

生成物 1

HCID 900229913-(4-(dihexylamino)-3-fluorophenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one収率 26.3%

試薬・触媒・溶媒 2

HCID 11026
Titanium isopropoxide
触媒
HCID 7237O-Xylene溶媒

反応条件

温度
165 °C

実験手順

To a mixture of N-(4-(dihexylamino)-3-fluorophenyl)-3-oxobutanamide (2.67 g, 7.05 mmol), and 2-(3-fluorophenoxy)acetamide (2.37 g, 14.0 mmol) in xylene (20 mL) was added titanium tetraisopropanolate (5.97 g, 21.0 mmol) and the mixture was stirred at 165° C. for 24 h. The mixture was cooled to rt and 120 mL of toluene and 150 mL of saturated NH4Cl aqueous solution were added. The resulting mixture stirred at rt overnight and filtered and the filtrate was extracted with DCM (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (0.95 g, 26%). The compound was characterized by the following spectroscopic data:

後処理

  1. temperatureThe mixture was cooled to rt
  2. stirringThe resulting mixture stirred at rt overnight
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with DCM (150 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

出典と根拠

ORDレコード
ord-9902e8b2ed2545069c8091b007c15faf
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434695B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート