Hydrogen Bromide → 3-(3-Methyl-4-{5-[2-oxo-2-(4-trifluoromethylphenyl)ethyl]pyridin-2-yloxy}phenyl)-1-piperonyltetrahydropyrimidin-2-one hydrobromide

HRID 884179ノート

反応式

HRID 884179 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]4[CH:30]=[CH:29][C:28]5[O:27][CH2:26][O:25][C:24]=5[CH:23]=4)[C:16]3=[O:31])=[CH:11][C:10]=2[CH3:32])=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[F:75][C:76]([F:87])([F:86])[C:77]1[CH:82]=[CH:81][C:80]([C:83](=[O:85])[CH3:84])=[CH:79][CH:78]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[BrH:1].[CH3:32][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:30]=[CH:29][C:28]4[O:27][CH2:26][O:25][C:24]=4[CH:23]=3)[C:16]2=[O:31])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:4]=[CH:3][C:2]([CH2:84][C:83](=[O:85])[C:80]2[CH:79]=[CH:78][C:77]([C:76]([F:75])([F:86])[F:87])=[CH:82][CH:81]=2)=[CH:7][N:6]=1

参加物

9

反応物 5

HCID 260Hydrogen BromideHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 3251421Potassium bis(trimethylsilyl)amideHCID 685273963-[4-(5-Bromopyridin-2-yloxy)-3-methylphenyl]-1-piperonyltetrahydropyrimidin-2-one

生成物 1

HCID 685269463-(3-Methyl-4-{5-[2-oxo-2-(4-trifluoromethylphenyl)ethyl]pyridin-2-yloxy}phenyl)-1-piperonyltetrahydropyrimidin-2-one hydrobromide収率 33.2%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 3-[4-(5-bromopyridin-2-yloxy)-3-methylphenyl]-1-piperonyltetrahydropyrimidin-2-one (0.11 g, 0.22 mmol) in toluene (10 mL) were added Pd2(dba)3 (10 mg, 0.01 mmol) and Xantphos (15 mg, 0.03 mmol) under a nitrogen atmosphere. The resulting solution was stirred for 5 minutes, and then 4′-(trifluoromethyl)acetophenone (63 mg, 0.33 mmol) and potassium bis(trimethylsilyl)amide (66 mg, 0.33 mmol) were added to the reaction % solution. The resulting solution was stirred at 70 to 80° C. for 30 minutes, and left to cool. Water was added to the reaction solution, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1), to yield 50 mg of a free form. To this free form was added an equivalent amount of hydrobromic acid, to thereby yield 50 mg of the title compound.

後処理

  1. stirringThe resulting solution was stirred at 70 to 80° C. for 30 minutes
  2. waitleft
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)
  8. customto yield 50 mg of a free form

出典と根拠

ORDレコード
ord-47e666046fbd40ab96f6f378cf31db05
出典データセット
uspto-grants-2012_08
特許番号
US08236826B2

反応ノート

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