Hydrogen Bromide → HCID 86267409、化合物

HRID 709988ノート

反応式

HRID 709988 の反応式
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([NH:29][CH3:30])[N:4]=1.Br>C(O)(=O)C>[CH3:28][C:11]1[N:10]=[C:9]([C:8]2[C:3](=[O:2])[NH:4][C:5]([NH:29][CH3:30])=[N:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[CH:17]=1

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 90416670HCID 90416670、化合物

生成物 1

HCID 86267409HCID 86267409、化合物収率 53.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

A solution of 4-methoxy-N-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.10 g, 0.25 mmol) in acetic acid (5 mL) was treated with HBr (0.12 mL, 1.0 mmol) and heated at 90° C. for 4 h. The mixture was cooled to RT, quenched with ice water, treated with NaHCO3 and NaCl, and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness, the resulting material treated with MeCN (3 mL) and the solid was collected via filtration to afford 5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(methylamino)pyrimidin-4(3H)-one (52 mg, 53%). 1H NMR (400 MHz, DMSO-d6): δ 11.26 (s, 1H), 8.70 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.28 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.70 (br s, 1H), 6.61 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 2.85 (d, J=4.7 Hz, 3H), 2.35 (s, 3H); MS (ESI) m/z: 390.2 (M+H+).

後処理

  1. temperatureThe mixture was cooled to RT
  2. customquenched with ice water
  3. additiontreated with NaHCO3 and NaCl
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionthe resulting material treated with MeCN (3 mL)
  8. filtrationthe solid was collected via filtration

出典と根拠

ORDレコード
ord-25ccce6cccbd4fe8aba6390b2a124e45
出典データセット
uspto-grants-2015_11
特許番号
US09181223B2

反応ノート

読み込み中…