Ethyl acetate hexane → HCID 86724339、化合物

HRID 1482683ノート

反応式

HRID 1482683 の反応式
[F:1][C:2]1[C:3]([NH:21][C:22]2[CH:23]=[C:24]([NH:28]C(=O)OC(C)(C)C)[CH:25]=[CH:26][CH:27]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=2)=[N:6][CH:7]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[NH2:28][C:24]1[CH:23]=[C:22]([NH:21][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=3)[N:4]=2)[CH:27]=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 21226206Ethyl acetate hexaneHCID 86724338Tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate

生成物 1

HCID 86724339HCID 86724339、化合物収率 91.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate (0.240 g) in DCM (5.0 mL) TFA (2.0 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes followed by stirring at room temperature for 30 minutes. The reaction was monitored by TLC using ethyl acetate:hexane (7:3) as mobile phase. After completion of the reaction, the mixture was quenched in water and basified with saturated sodium bicarbonate solution. Product was extracted into DCM. The organic layer was washed with brine and dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. The obtained solid was purified by trituration with ether to give 0.175 g of 5-((4-((3-aminophenyl)amino)-5-fluoropyrimidin-2-yl)amino)-2-(2-methoxyethoxy)phenol. 1H NMR: DMSO-d6 (400 MHz): 3.282 (s, 3H), 3.617-3.640 (t, 2H, J=4.4), 4.004-4.040 (t, 2H, J=4.4), 4.992 (s, 2H), 6.306-6.316 (d, 1H, J=3.2), 6.772-6.793 (d, 1H, J=8.4), 6.952-7.042 (m, 3H), 7.095 (s, 1H), 7.187 (s, 1H), 8.004-8.013 (d, 1H, J=3.6), 8.811 (s, 1H), 8.861 (s, 1H), 9.001 (s, 1H).

後処理

  1. stirringby stirring at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. customthe mixture was quenched in water and basified with saturated sodium bicarbonate solution
  4. extractionProduct was extracted into DCM
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely
  8. customat 40° C
  9. customThe obtained solid was purified by trituration with ether

出典と根拠

ORDレコード
ord-33bb41b3bc914b50a4de73acb894d791
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

読み込み中…