Dimethylformamide → 1,3-Dimethyl-5-triisopropylsilanyloxy-tetrahydro-pyrimidin-2-one

HRID 2204323노트

반응식

HRID 2204323 반응식
[H-].[Na+].[CH:3]([Si:6]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[O:7][CH:8]1CN[C:11](=O)[NH:10][CH2:9]1)([CH3:5])[CH3:4].CI.[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>>[CH3:23][N:24]1[CH2:25][CH:8]([O:7][Si:6]([CH:15]([CH3:17])[CH3:16])([CH:3]([CH3:5])[CH3:4])[CH:18]([CH3:19])[CH3:20])[CH2:9][N:10]([CH3:11])[C:26]1=[O:27]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 867031315-Triisopropylsilanyloxy-tetrahydro-pyrimidin-2-one

생성물 1

HCID 867031301,3-Dimethyl-5-triisopropylsilanyloxy-tetrahydro-pyrimidin-2-one

실험 절차

NaH (141 mmol) was added portionwise to a solution of 5-triisopropylsilanyloxy-tetrahydro-pyrimidin-2-one (Step P9) (28.2 mmol) in DMF (200 mL) at 0° C. After 15 min, the reaction was warmed to rt. After 2 h, the mixture was cooled to 0° C., treated with methyl iodide (197 mmol) and then allowed to warm to rt overnight. The reaction mixture was quenched by addition of water and extracted with toluene. The aqueous layer was washed with EtOAc. The combined organic layers were washed with a saturated aqueous NaHCO3 solution, dried (Na2SO4), filtered, and concentrated. The residue was used without further purification. ESI-MS: tR=1.33 min, [M+H]+ 301.3 (LC-MS 1).

후처리

  1. waitAfter 2 h
  2. temperaturethe mixture was cooled to 0° C.
  3. temperatureto warm to rt overnight
  4. customThe reaction mixture was quenched by addition of water
  5. extractionextracted with toluene
  6. washThe aqueous layer was washed with EtOAc
  7. washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was used without further purification

출처 및 근거

ORD 기록
ord-33f09629675a4e81b359830564011222
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365576B2

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