N-bromobutanimide → HCID 67328038、化合物

HRID 1846195ノート

反応式

HRID 1846195 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22])[N:6]=[C:5]([N:23]([CH3:25])[CH3:24])[N:4]=1.[Br:26]N1C(=O)CCC1=O>C(#N)C>[Br:26][C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([N:23]([CH3:25])[CH3:24])=[N:6][C:7]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 67329285HCID 67329285、化合物

生成物 1

HCID 67328038HCID 67328038、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution containing 1.41 g (3.99 mmol) of 4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyrimidin-2-amine in 10 mL of acetonitrile were added 852 mg (4.79 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23° C. and protected from light for 5 h. The reaction mixture was concentrated under diminished pressure and the residue was dissolved into 100 mL of ethyl acetate. The organic solution was washed with a 100-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with 9:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 910 mg (53%); silica gel TLC Rf 0.65 (9:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.31-1.26 (br m, 10H), 1.54-1.64 (m, 4H), 2.67 (dd, 2H, J=7.6, 7.6 Hz), 3.11 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.92 (s, 3H) and 4.59 (s, 2H); 13C-NMR (CDCL3) δ 26.18, 27.59, 29.34, 29.40, 29.40, 29.47, 29.55, 29.72, 36.68, 36.93, 53.96, 55.04, 67.85, 91.16, 96.35, 160.06, 165.05 and 169.04; mass spectrum (APCI+), m/z 432.1857 (M+H) (C19H35N3O3Br requires 432.1862).

後処理

  1. concentrationThe reaction mixture was concentrated under diminished pressure
  2. dissolutionthe residue was dissolved into 100 mL of ethyl acetate
  3. washThe organic solution was washed with a 100-mL portion of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column
  7. washElution with 9:1 hexanes-ethyl acetate

出典と根拠

ORDレコード
ord-548dc3a260ce4420ac4968b7aa334c8e
出典データセット
uspto-grants-2015_02
特許番号
US08952025B2

反応ノート

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