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

HRID 410397

反応式

HRID 410397 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-abe2bfbf816c4806a6307bbea021658e
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

関連ノート

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