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

HRID 1668388노트

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HRID 1668388 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516920Potassium bisulfate용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6eec38c3d55a4051b7d7acf21c16c250
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989445B2

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