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Potassium Carbonate → 3-[4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester

HRID 2172606
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HRID 2172606 반응식
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[N:13]=[C:12]2[CH3:19])[CH:5]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH3:21])[CH:24]=3)[N:13]=[C:12]2[CH3:19])[CH:5]=1
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참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 40672073-Methoxybenzyl bromideHCID 1363878053-(4-hydroxy-2-methyl-6-oxo-6H-pyrimidin-1-yl)-4-methyl-benzoic acid methyl ester

생성물 1

HCID 866862913-[4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester수율 34.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of Intermediate 2 (460 mg, 1.68 mmol) in N,N-dimethylformamide (2 mL) was added 3-methoxybenzyl bromide (0.23 mL, 1.68 mmol), potassium carbonate (350 mg, 2.53 mmol) and 18-crown-6 (40 mg). The slurry was stirred at ambient temperature for one hour. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a white semi-solid (226 mg, 34% yield). MS (M+H): 395

후처리

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe slurry was filtered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified

출처 및 근거

ORD 기록
ord-3221739330d6428f803419c4ef925b27
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056110B2

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