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

HRID 12662

反応式

HRID 12662 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-02bf8d507037412cb69175d867be4cb6
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

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