Tetraethyl orthocarbonate → 4-(6-Bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine

HRID 1398641ノート

反応式

HRID 1398641 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.[CH2:17]([O:19][C:20](OCC)(OCC)OCC)[CH3:18]>C(O)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([O:19][CH2:17][CH3:18])[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:3]=2[CH:4]=1

参加物

4

反応物 2

HCID 66213Tetraethyl orthocarbonateHCID 681818104-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

生成物 1

HCID 681818044-(6-Bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (652 mg, 1.98 mmol), (triethoxymethoxy)ethane (2.0 mL, 9.89 mmol) and acetic acid (0.09 mL) was heated at 80° C. for 40 minutes. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and washed with saturated aqueous sodium hydrogencarbonate (2×10 mL) and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the crude product as an orange solid 1H NMR (500 MHz, CDCl3) delta 1.55 (3H, t, J=7.09 Hz), 4.71 (2H, q, J=7.25 Hz), 5.21 (2H, br. s.), 7.13 (1H, d, J=5.67 Hz), 7.35-7.42 (2H, m), 8.36-8.40 (2H, m); LC-MS: m/z=+334.00/335.75 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (5 mL)
  4. washwashed with saturated aqueous sodium hydrogencarbonate (2×10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-466ae22c45cc449099bda769b485e92d
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

読み込み中…