Diisopropylethylamine → Methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

HRID 2353323노트

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HRID 2353323 반응식
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH2:27].C(N(CC)C(C)C)(C)C>O1CCOCC1>[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH:27][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 57542076Methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

생성물 1

HCID 57542083Methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate수율 74%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

To a solution of methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.70 g, 8.39 mmol) and aminoacetoaldehyde dimethyl acetal (1.83 mL, 16.78 mmol) in dioxane (40 mL) was added N,N-diisopropylethylamine (1.46 mL, 8.39 mmol). The mixture was stirred at 85° C. for 1 day. After cooling to room temperature, the reaction was quenched with water, and extracted with ethyl acetate. The extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica-gel, (ethyl acetate) to give methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)-pyrimidin-5-yl]acetate (2.41 g, 74%) as brown oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica-gel, (ethyl acetate)

출처 및 근거

ORD 기록
ord-a87927881036477bb026a80bfce37c20
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750014B2

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