Sodium hydride → HCID 59808428、化合物

HRID 1010578

反応式

HRID 1010578 の反応式
[H-].[Na+].[I:3]C1NC=CN=1.Cl[CH2:10][CH2:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13].C[N:24]1[CH2:29]CC[N:26]([CH3:30])[C:25]1=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:3][C:30]1[N:26]=[CH:25][N:24]([CH2:10][CH2:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13])[CH:29]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-2 回HCID 27734682-iodo-1H-imidazoleHCID 57429079tert-butyl N-(4-chloro-2-methylbutan-2-yl)carbamate

生成物 1

HCID 59808428HCID 59808428、化合物収率 42%

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

反応条件

温度
0 °C

実験手順

0.556 g (22.0 mmol) sodium hydride were added batchwise to a solution of 3.88 g (20.0 mmol) iodoimidazole in 30 mL 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone at 5° C. with vigorous stirring. After the development of gas had ended the reaction was stirred for 1 h at 0° C. and 4.44 g (20 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate in 5 mL 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone and 0.739 g (2.00 mmol) tetrabutylammonium iodide were added. The reaction mixture was stirred for 16 h at ambient temperature, stirred for 24 h at 80° C., cooled to ambient temperature and poured into 750 mL ice water/ethyl acetate 2:1. The phases were separated and the aqueous phase was extracted three times with 150 mL ethyl acetate. The combined organic phases were washed five times with 150 mL water, then once with 150 mL saturated, aqueous sodium chloride solution, dried over sodium sulphate and the solvent was eliminated using the rotary evaporator. The residue was purified by flash column chromatography [petroleum ether/ethyl acetate (80:20→0:100)]. 3.19 g (8.40 mmol, 42%) tert-butyl [3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propyl]-carbamate were obtained as a colourless oil.

後処理

  1. stirringThe reaction mixture was stirred for 16 h at ambient temperature
  2. stirringstirred for 24 h at 80° C.
  3. temperaturecooled to ambient temperature
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted three times with 150 mL ethyl acetate
  6. washThe combined organic phases were washed five times with 150 mL water
  7. dry with materialonce with 150 mL saturated, aqueous sodium chloride solution, dried over sodium sulphate
  8. customthe rotary evaporator
  9. customThe residue was purified by flash column chromatography [petroleum ether/ethyl acetate (80:20→0:100)]

出典と根拠

ORDレコード
ord-f17c85d8c81648609559f3b4f4f96cb9
出典データセット
uspto-grants-2011_07
特許番号
US07977334B2

関連ノート

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