Sodium hydride → 1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

HRID 12662

반응식

HRID 12662 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[C:25]([Si:22]([CH3:24])([CH3:23])[O:21][CH2:20][CH2:19][CH2:18][N:11]1[CH:12]=[C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])[C:8](=[O:14])[NH:9][C:10]1=[O:13])([CH3:28])([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 149145925-(3-Methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

생성물 1

HCID 686913001-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione수율 37%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a suspension of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep26, 110 mg, 0.52 mmol) in dry DMF (10 mL), 60% NaH (31 mg, 0.78 mmol) was added. The mixture was then heated at 100° C. for 1 hour. (3-bromo-propoxy)-tert-butyl-dimethyl-silane (180 μl, 0.7 mmol) was then added at room temperature and the reaction was stirred overnight. The solvent was evaporated and the crude was partitioned between NaHCO3 and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give the title compound as a white solid (73 mg, 37% yield).

후처리

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe crude was partitioned between NaHCO3 and Et2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8)

출처 및 근거

ORD 기록
ord-02bf8d507037412cb69175d867be4cb6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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