Tert-butyl (3-((2-((3-(benzyloxy)-4-(2-methoxyethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate → Tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate

HRID 1482682ノート

反応式

HRID 1482682 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:29]=[C:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:31]=[CH:32][CH:33]=3)[C:24]([F:42])=[CH:23][N:22]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][O:18][CH3:19])C1C=CC=CC=1>[Pd].C(O)C>[F:42][C:24]1[C:25]([NH:27][C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH:31]=[CH:32][CH:33]=2)=[N:26][C:21]([NH:20][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:9]([OH:8])[CH:10]=2)=[N:22][CH:23]=1

参加物

4

反応物 1

HCID 86724337Tert-butyl (3-((2-((3-(benzyloxy)-4-(2-methoxyethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate

生成物 1

HCID 86724338Tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate収率 81.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

In a 100 mL Autoclave, Pd—C (0.035 g) and ethanol were charged. tert-butyl (3-((2-((3-(benzyloxy)-4-(2-methoxyethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate (0.35 g) was added to the above reaction mixture, and the autoclave was flushed with nitrogen. Hydrogen pressure (140 psi) was applied and reaction mixture was stirred at room temperature for 50 hr. After completion, the reaction mixture was filtered using Celite and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure at 40° C. to give 0.240 g of tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate. 1H NMR: DMSO-d6 (400 MHz): 1.475 (s, 9H), 3.316 (s, 3H), 3.618-3.641 (t, 2H, J=4.4), 4.028-4.050 (t, 2H, J=4.4), 6.732-6.753 (d, 1H, J=8.4), 7.075-7.097 (m, 2H), 7.141-7.208 (m, 2H), 7.476-7.495 (d, 1H, J=7.6), 7.851 (s, 1H), 8.036-8.045 (d, 1H, J=3.6), 8.784-8.796 (d, 2H, J=4.8), 9.260-9.301 (d, 2H, J=16.4).

後処理

  1. customthe autoclave was flushed with nitrogen
  2. customreaction mixture
  3. filtrationAfter completion, the reaction mixture was filtered
  4. washthe filter cake was washed with ethanol
  5. concentrationThe filtrate was concentrated under reduced pressure at 40° C.

出典と根拠

ORDレコード
ord-a33fe26b7d154365b80713313f728941
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…