Potassium Carbonate → (S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052700ノート

反応式

HRID 1052700 の反応式
Br[C:2]1[S:30][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C@H:11]([C:13]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17](=[O:25])[C:16]4=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]4[N:14]=3)[CH3:12])[C:4]=2[CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.[Cl-].[NH4+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][C:26]1[CH:27]=[CH:28][N:15]2[C:16]=1[C:17](=[O:25])[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([C@@H:11]([NH:10][C:9]1[C:4]3[CH:3]=[C:2]([CH3:31])[S:30][C:5]=3[N:6]=[CH:7][N:8]=1)[CH3:12])=[N:14]2

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 574072TrimethylboroxineHCID 118433746(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

生成物 1

HCID 73776064(S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.10 mmol) was dissolved in 3 mL dimethylformamide. Potassium carbonate (287 mg, 2.08 mmol), tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) and trimethylboroxine (130 μl, 0.93 mmol) were added under argon conditions. The reaction mixture was stirred at 130° C. for 2 h. The crude was poured into 25 mL saturated ammonium chloride solution and extracted twice with ethyl acetate. The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System by reverse phase to obtain 26 mg (60% yield) of a yellow solid as a title compound. Purity 100%.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organics were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified
  6. customSP1® Purification System by reverse phase

出典と根拠

ORDレコード
ord-50ef15b0677243fd9ca87d6588badaa6
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

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