Triphenylphosphine → methyl (E)-3-(2-{3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]phenyl}pyrimidin-5-yl)acrylate

HRID 1408397ノート

反応式

HRID 1408397 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].O[CH2:18][C:19]1[CH:20]=[C:21]([C:25]2[N:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34])=[CH:27][N:26]=2)[CH:22]=[CH:23][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:16]=[C:13]1[N:14]([CH2:18][C:19]2[CH:20]=[C:21]([C:25]3[N:26]=[CH:27][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34])=[CH:29][N:30]=3)[CH:22]=[CH:23][CH:24]=2)[N:15]=[C:10]([C:4]2[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[CH:11]=[CH:12]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58289762methyl (E)-3-[2-(3-hydroxymethylphenyl)pyrimidin-5-yl]acrylateHCID 594068096-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one

生成物 1

HCID 59484916methyl (E)-3-(2-{3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]phenyl}pyrimidin-5-yl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

47.2 90 mg (0.4 mmol) of 6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one and 111 mg (0.41 mmol) of methyl (E)-3-[2-(3-hydroxymethylphenyl)-pyrimidin-5-yl]acrylate are suspended in 3 ml of THF with 200 mg (0.6 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g), and the mixture is shaken at room temperature for 30 min. The mixture is cooled to 0° C., and 95 μl (0.6 mmol) of diethyl azodicarboxylate are added. The reaction mixture is shaken at room temperature for 24 h. The reaction mixture is purified by means of preparative HPLC; yield: 7 mg of “A283”; HPLC: Rt=3.41 min (method C);

後処理

  1. temperatureThe mixture is cooled to 0° C.
  2. stirringThe reaction mixture is shaken at room temperature for 24 h
  3. customThe reaction mixture is purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-85d8995e7a5043998b0aa0553126da58
出典データセット
uspto-grants-2014_12
特許番号
US08921357B2

反応ノート

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