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Methanesulfonic Acid → N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 410405
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HRID 410405 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1)[NH2:5].Cl[C:13]1[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=1.CS(O)(=O)=O>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13]2[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1
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참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 672489413-Bromo-5-(methoxymethyl)aniline

생성물 1

HCID 67429779N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine수율 72.6%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매
HCID 31275
1,4-Dioxane
용매

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온도
100 °C

실험 절차

To a solution of the product of Step 2 (258 mg, 1.194 mmol) in dioxane (3.8 mL) were added 2-chloro-4-(trifluoromethyl)pyrimidine (251 mg, 1.373 mmol) and methanesulfonic acid (0.07 mL, 1.015 mmol). The reaction was then stirred overnight at 100° C. The reaction was then cooled, diluted with ethyl acetate and then washed with brine solution. The organic layer was collected, dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo. Flash chromatography (hexane/ethyl acetate: 70/30) was used for purification to afford N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine as an off-white solid (314 mg, 0.867 mmol, 72.6% yield). MS ESI: [M+H]+ m/z=362.0.

후처리

  1. temperatureThe reaction was then cooled
  2. washwashed with brine solution
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customEthyl acetate was then removed in vacuo
  7. customFlash chromatography (hexane/ethyl acetate: 70/30) was used for purification

출처 및 근거

ORD 기록
ord-bb47d888eb3a4b758df0d82ede5281a7
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759366B2

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