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Allyl bromide → 1,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1788752
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HRID 1788752 반응식
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:4]([CH2:33][CH:32]=[CH2:31])[CH:5]([CH3:24])[C:6]([C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

생성물 1

HCID 571142891,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester수율 58.9%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (4.0 g, 12.0 mmol; see Example 1A) in dry dimethylformamide (10 ml) was treated with finely ground potassium carbonate (6.6 g, 48.0 mmoles) and allyl bromide (1.7 ml, 20.0 mmole). The resulting suspension was allowed to stir under argon at room temperature for 10 hours. The reaction was diluted with ethyl acetate, filtered and the filtrate was washed with water and brine. It was dried over anhydrous magnesium sulfate and evaporated to provide a yellow oil. Purification by flash chromatography (20% ethyl acetate in hexanes) yielded the title compound (2.64 g) as a yellow oil.

후처리

  1. filtrationfiltered
  2. washthe filtrate was washed with water and brine
  3. dry with materialIt was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto provide a yellow oil
  6. customPurification by flash chromatography (20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-149ebce89605495e8a96c6b0c1e5b343
출처 데이터셋
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04684655

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