Methanesulfonic Acid → 4-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

HRID 410397

반응식

HRID 410397 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[O:3]1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1.O1CCOCC1.CS(O)(=O)=O>C(OCC)(=O)C>[CH3:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:10]=2)[N:23]=1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 312751,4-DioxaneHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 116296072-Chloro-4-methylpyrimidine

생성물 1

HCID 584563194-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine수율 58%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a flask containing 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.50 g, 6.85 mmol) and 2-chloro-4-methylpyrimidine (1.01 g, 7.87 mmol) were added dioxane (69 mL) and methanesulfonic acid (0.51 mL, 7.87 mmol). The reaction was heated at 100° C. overnight. The reaction was then cooled to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield 4-methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (1.23 g, 3.95 mmol, 58% yield). MS ESI: [M+H]+ m/z 312. 1H NMR (500 MHz, DMSO-d6) δ 9.48 (s, 1H), 8.30 (d, J=5.0, 1H), 7.98 (d, J=8.0, 1H), 7.95 (s, 1H), 7.29-7.20 (m, 2H), 6.71 (d, J=5:0, 1H), 2.33 (s, 3H), 1.28 (s, 12H).

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFlash chromatography was used for purification

출처 및 근거

ORD 기록
ord-abe2bfbf816c4806a6307bbea021658e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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