Dimethylformamide → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N',N'-trimethylthiourea

HRID 1668388ノート

反応式

HRID 1668388 の反応式
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25](CNC)=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[S:34].[CH2:37]([N:39](CC)[CH2:40]C)C.CN(C)C=O>C(OCC)(=O)C.S([O-])(O)(=O)=O.[K+]>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:31][N:32]([CH3:36])[C:33]([N:39]([CH3:40])[CH3:37])=[S:34])=[CH:26][CH:27]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

生成物 1

HCID 11999424N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N',N'-trimethylthiourea収率 39.8%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 516920Potassium bisulfate溶媒

反応条件

温度
60 °C

実験手順

A mixture of the compound (0.1 g) obtained in Example 4, dimethylcarbamothioyl chloride (25 mg), triethylamine (76 mg) and N,N-dimethylformamide (2 ml) was stirred at 60° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, 5% aqueous potassium hydrogen sulfate solution, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and is concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (3:1, volume ratio)], and recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (40 mg) as a colorless powder.

後処理

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationis concentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (3:1, volume ratio)]
  5. customrecrystallized from ethyl acetate-hexane (1:1, volume ratio)

出典と根拠

ORDレコード
ord-6eec38c3d55a4051b7d7acf21c16c250
出典データセット
uspto-grants-2011_08
特許番号
US07989445B2

反応ノート

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