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 2274265노트

반응식

HRID 2274265 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-cc3581fd88d9440ea4e98c4b9e7d97e7
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126950B2

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